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Chemical Structure| 4254-15-3 Chemical Structure| 4254-15-3
Chemical Structure| 4254-15-3

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CAS No.: 4254-15-3

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(S)-(+)-1,2-Propanediol is an endogenous metabolite.

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Product Details of (S)-(+)-1,2-Propanediol

CAS No. :4254-15-3
Formula : C3H8O2
M.W : 76.09
SMILES Code : C[C@H](O)CO
MDL No. :MFCD00004539
InChI Key :DNIAPMSPPWPWGF-VKHMYHEASA-N
Pubchem ID :439846

Safety of (S)-(+)-1,2-Propanediol

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

Application In Synthesis of (S)-(+)-1,2-Propanediol

* 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 [ 4254-15-3 ]

[ 4254-15-3 ] Synthesis Path-Downstream   1~5

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YieldReaction ConditionsOperation in experiment
With p-toluenesulfonic acid monohydrate; In hexane; toluene; COMPARATIVE EXAMPLE 1 Synthesis of chiral 2-methyl-2,3-dihydro-thieno[3,4-b] [1,4]dioxine A solution of <strong>[51792-34-8]3,4-dimethoxythiophene</strong> (5.18 g), (S)-1,2-propanediol (3.0 g) and p-toluenesulfonic acid monohydrate (100 mg) in toluene (50 ml) was heated at 95° C. during which a continuous stream of nitrogen was passed over the solution. After 30 h the reaction mixture was poured into ethyl acetate, washed with NaHCO3 and the organic phase was concentrated. Subsequent filtration over SiO2 using n-hexane as eluant resulted in pure product (3.90 g). GC-MS: 156 (purity>99percent); 1H-NMR (CDCl3): delta 6.30 (2*d, 2H), 4.26 (m, 1H), 4.15 (dd, 1H), 3.82 (dd, 1H), 1.35 (d, 3H) ppm; specific rotation [alpha]=-46° at 25° C. and 436 nm in hexane (c=0.066).
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YieldReaction ConditionsOperation in experiment
With dmap; potassium hydroxide; triethylamine; In dichloromethane; (c) (S)-(-)-1-Benzyloxy-2propanol A mixture of powdered KOH (5.90 g, 105 mmol), (S)-(+)-1,2-propanediol (8.00 g, 105 mmol) and benzyl chloride (13.3 g, 105 mmol) was heated at 130 C. for 2 hours. The mixture was cooled to room temperature, diluted with water and extracted with Et2 O layer was separated and washed with brine, dried over MgSO4, filtered and concentrated to provide 14.49 g of crude product which was dissolved in dichloromethane (50 mL). Triethyl amine (4.90 g, 48.4 mmol), DMAP (0.48 g, 3.93 mmol) and tert-butyldimethylsilyl chloride (6.5 g, 43.2 mmol) were added and the resulting solution was stirred at room temperature ca. 18 hours. The solution was then washed with H2 O and brine, dried over MgSO4, filtered and concentrated in vacuo providing a crude oil. Flash chromatography on silica gel eluding with 27.5% EtOAc/hexanes provided (s)-(-)-1-Benzyloxy-2-propanol (4.12 g, 24.8 mmol, 24%) as a nearly colorless oil: [alpha]D20 =+5.36 (c=3.30, MeOH); 1 H NMR (CDCl3) delta 7.4-7.3 (5H, m), 4.56 (2H, s), 4.01 (1H, ddq, J=8.2, 6.3, 3), 3.48 (1H, dd, J=9.3, 3), 3.28 (1H, dd, J=9.3, 8.2), 2.05 (1H, br), 1.15 (3H, d, J=6.3); CIMS m/z 189 (M+23, 100); Anal. Calcd for C10 H14 O2.circle-solid.(0.1 H2 O): C, 71.49; H, 8.52; Found: C, 71.34; H, 8.51.
 

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