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Chemical Structure| 2012-74-0 Chemical Structure| 2012-74-0
Chemical Structure| 2012-74-0

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CAS No.: 2012-74-0

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Product Details of 2-(4-Chlorophenyl)-3-methylbutyric Acid

CAS No. :2012-74-0
Formula : C11H13ClO2
M.W : 212.67
SMILES Code : CC(C)C(C(O)=O)C1=CC=C(Cl)C=C1
MDL No. :MFCD00037763
InChI Key :VTJMSIIXXKNIDJ-UHFFFAOYSA-N
Pubchem ID :16197

Safety of 2-(4-Chlorophenyl)-3-methylbutyric Acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 2-(4-Chlorophenyl)-3-methylbutyric Acid

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 2012-74-0 ]

[ 2012-74-0 ] Synthesis Path-Downstream   1~32

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  • [ 2012-81-9 ]
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  • [ 51631-50-6 ]
  • 3
  • [ 2012-74-0 ]
  • (+)-2-(4-chlorophenyl)-3-methylbutanoic acid [ No CAS ]
  • 4
  • [ 2012-74-0 ]
  • (-)-2-(4-chlorophenyl)-3-methylbutanoic acid [ No CAS ]
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  • [ 5096-11-7 ]
  • [ 51631-99-3 ]
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  • [ 88549-73-9 ]
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  • [ 74408-48-3 ]
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YieldReaction ConditionsOperation in experiment
With potassium permanganate; sulfuric acid; In toluene; EXAMPLE 12 Preparation of 2-(4-chlorophenyl)-3-methylbutyric acid 100 g (0.49 mol) of 96.42% by weight 2-(4-chlorophenyl)-3-methylbutanal (the product of Example 11) and 558.4 g of 19.4% by weight sulfuric acid are initially introduced into a 1 liter three-necked flask fitted with a stirrer, a reflux condenser, a dropping funnel, and an internal thermometer. Thereto, 79.05 g (0.5 mol) of KMnO4 are added at 20 to 25 C. in the course of 2 hours. After an after-reaction of one hour at 20 to 25 C., 600 g of toluene are introduced. The solid is filtered off and the organic phase is separated from the aqueous phase. The organic phase is freed from the toluene on a rotary evaporator and the residue is recrystallized from cyclohexane. The yield is 86.4 g corresponding to 82.8% of theoretical (based on the aldehyde employed), and the product has a melding point of 89 to 91 C.
YieldReaction ConditionsOperation in experiment
EXAMPLE 5 5.30 g of (-)-isomer rich alpha-isopropyl-4-chlorophenylacetic acid ([alpha]D24 -46.56) was mixed with 2.10 g of potassium hydroxide and 50 ml of ethylene glycol, and the resulting mixture was kept at 170 C. for 15 hours. The reaction solution was cooled to room temperature, diluted with 250 ml of water and acidified to a pH of 1 with concentrated hydrochloric acid. Thereafter, the same procedure as in Example 1 was carried out to obtain 5.19 g of racemized alpha-isopropyl-4-chlorophenylacetic acid. The rate of conversion was about 95%. [alpha]D22.0 -2.07.
STEP D: D 2-isopropyl-2-p-chlorophenyl-acetic acid 286 ml of 2 N aqueous hydrochloric acid were added with stirring to a mixture of 143 g of the product of Step C and 286 ml of methylene chloride and the mixture was stirred for 15 minutes resulting in 2 limpid phases. The decanted aqueous phase was extracted with methylene chloride and the combined organic phases were washed with water. The aqueous wash waters were extracted with methylene chloride and the organic phases were dried and filtered. The filtrate was evaporated to dryness to obtain 91 g of D 2-isopropyl-2-p-chlorophenyl-acetic acid melting at 105 C. and having a specific rotation of [alpha]D20 =+42 (c=1% in ethanol).
Suitable examples of the substituted phenyl-acetic acids of the formula (II) are exemplified as follows. ... 4-Methoxy-alpha-iso-propyl-phenylacetic acid 4-Chloro-alpha-ethyl-phenylacetic acid 4-Chloro-alpha-iso-propyl-phenylacetic acid 4-Bromo-alpha-iso-propyl phenylacetic acid ...
  • 11
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  • [ 186347-51-3 ]
  • 2-(4-chloro-phenyl)-<i>N</i>-[3-(4-cyano-4-<i>o</i>-tolyl-piperidin-1-yl)-propyl]-3-methyl-butyramide [ No CAS ]
  • 13
  • [ 51630-58-1 ]
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  • [ 39515-47-4 ]
  • 14
  • [ 67-56-1 ]
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  • [ 86618-06-6 ]
YieldReaction ConditionsOperation in experiment
100% sulfuric acid; at 20℃; To a solution of commercial <strong>[2012-74-0]2-(4-chlorophenyl)-3-methylbutyric acid</strong> (1 g, 4.7 mmol) in CH3OH (10 mL), few drops of cone. H2SO4 were added, and the resulting mixture was left stirring at room temperature overnight. After solvent evaporation under vacuum, CH2Cl2 (10 mL) and H2O (10 mL) were added; the two phases were separated and the organic one dried over Na2SO4, filtered and evaporated under vacuum to give the intermediate methyl 2-(4-chlorophenyl)-3-methylbutanoate as an <n="18"/>oily residue (quantitative yield). This intermediate was transformed in the related methyl 2-(4-hydroxyphenyl)-3-methylbutanoate according a known procedure3: a mixture of methyl 2-(4-chlorophenyl)-3-methylbutanoate (1.06 g, 4.7 mmol), 60% sodium hydride (0.56 g, 14.1 mmol) and H2O (85 muL, 4.7 mmol) was heated to 45C while kept at argon atmosphere for 3 days (1H-NMR analysis). The solvent was evaporated and the residue diluted with EtOAc and washed with IN HCl (2 x 5 mL); the solvent was evaporated under vacuum and the crude residue was purified by flash chromatography (CHCI3/CH3OH 85: 15) to give the pure intermediate as an oil (0.75 g, 77% yield). 1H-NMR (CDCl3) delta 7.18 (d, 2H, J = 7Hz), 6.82 (d, 2H, J = 7Hz), 5.75 (bs, IH, OH), 3.70 (s, 3H), 3.15 (d, IH, J = 14Hz), 2.55 (m, IH), 1.10 (d, 3H, J = 7Hz), 0.72 (d, 3H, J = 7Hz). The steps of insertion of the triflate group and the following hydrolysis were performed as described1 and 3-methyl-2-[4- (trifluoromethylsulfonyloxy)phenyl]butanoic acid was obtained as a colourless oil (0.91 g, 78% yield calculated from the 4-hydroxy methyl ester derivative). The optical resolution was performed as described.4 (2R)-3-methyl-2-[4- (trifluoromethylsulfonyloxy)phenyl]butanoic acid (0.32 g, 35% yield) was obtained as a white solid. [alpha]D25 (c=l, CH3OH): -50; 1H-NMR (CDCl3) delta 7.55 (d, 2H, J = 7Hz), 7.25 (d, 2H, J = 7Hz), 3.15 (d, IH, J = 14Hz), 2.55 (m, IH), 1.10 (d, 3H, J = 7Hz), 0.72 (d, 3H, J = 7Hz).
  • 15
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  • [ 916074-16-3 ]
  • 16
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  • C11H20N3O3(C6H4Cl) [ No CAS ]
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  • C16H15N4OSCl3 [ No CAS ]
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  • C20H25N4O3SCl [ No CAS ]
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  • 2-amino-1-(4-chloro-phenyl)-3-methyl-butan-1-ol [ No CAS ]
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  • 26
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  • (S)-3-[cyano[(S)-2-(4-chlorophenyl)-3-methyl-1-oxobutanoxy]methyl]phenoxyacetic acid [ No CAS ]
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  • N-[(S)-4-chloro-2-(1-methylethyl)benzeneacetyl]4-amino-L-phenylalanine [ No CAS ]
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  • (S)-cyano[3-(4-aminophenoxy)phenyl]methyl (S)-4-chloro-α-(1-methylethyl)benzeneacetate [ No CAS ]
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  • (S)-cyano[3-(4-nitrophenoxy)phenyl]methyl (S)-4-chloro-α-(1-methylethyl)benzeneacetate [ No CAS ]
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  • (R)-cyano[3-(4-nitrophenoxy)phenyl]methyl (S)-4-chloro-α-(1-methylethyl)benzeneacetate [ No CAS ]
  • 32
  • [ 2012-74-0 ]
  • benzyl (S)-[cyano[(S)-2-(4-chlorophenyl)-3-methyl-1-oxobutanoxy]methyl]phenoxyacetate [ No CAS ]
 

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