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Chemical Structure| 274-09-9 Chemical Structure| 274-09-9
Chemical Structure| 274-09-9

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CAS No.: 274-09-9

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Product Details of 1,3-Benzodioxole

CAS No. :274-09-9
Formula : C7H6O2
M.W : 122.12
SMILES Code : C12=CC=CC=C1OCO2
MDL No. :MFCD00005818
InChI Key :FTNJQNQLEGKTGD-UHFFFAOYSA-N
Pubchem ID :9229

Safety of 1,3-Benzodioxole

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302+H332
Precautionary Statements:P261-P271

Application In Synthesis of 1,3-Benzodioxole

* 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.

  • Upstream synthesis route of [ 274-09-9 ]
  • Downstream synthetic route of [ 274-09-9 ]

[ 274-09-9 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 274-09-9 ]
  • [ 5768-39-8 ]
References: [1] Patent: US5886044, 1999, A, .
[2] Patent: US5780483, 1998, A, .
[3] Patent: US6262113, 2001, B1, .
  • 2
  • [ 274-09-9 ]
  • [ 124-38-9 ]
  • [ 5768-39-8 ]
  • [ 120-80-9 ]
References: [1] Chemistry - A European Journal, 2002, vol. 8, # 4, p. 799 - 804.
  • 3
  • [ 106-31-0 ]
  • [ 274-09-9 ]
  • [ 63740-97-6 ]
YieldReaction ConditionsOperation in experiment
85% With boron trifluoride diethyl etherate In 1,2-dichloro-ethane at -5℃; for 3.25 h; A pre-dried two-neck round bottom flask was charged with 1,2-methylenedioxy benzene (2.0 g, 16.37 mmol), 1,2-dichloroethane (7 mL) and n-butyric anhydride (3.2 mL, 19.6 mmol).
The resulting mixture was cooled to -10 °C, to that BF3·Et2O (6.78 g, 1.38 mmol) was added by slow addition over 15 min, while maintaining the temperature -5 °C to 0 °C.
After the addition, the reaction mixture was stirred at -5 °C for 3 h.
The reaction was then quenched with sodium acetate solution, the organic layer was separated and washed with 5percent NaOH (7 mL) followed by water.
The organic layers were concentrated and the crude product was purified by column chromatography using on silica gel with hexane/ethyl acetate (10percent) as eluent to yielded the desired compound 4 (1.34 g, 85percent).
1H NMR (400 MHz, CDCl3), 7.52 (dd, J=8.1, 1.6 Hz, 1H), 7.40 (d, J=8.1 Hz, 1H), 6.80 (d, J=8.1 Hz, 1H), 5.99 (s, 1H), 2.82 (t, J=7.3 Hz, 2H), 1.70 (h, J=7.4 Hz, 2H), 0.95 (t, J=7.4 Hz, 3H); 13C NMR (100 MHz, CDCl3) 198.4, 151.5, 148.1, 132.0, 124.1, 107.8, 107.7, 101.7, 40.2, 18.0, 13.8; HRMS-ESI-MS (m/z) [M+H]+: calcd for C11H13O3: 193.0865; found 193.0867.
References: [1] Organic Process Research and Development, 2002, vol. 6, # 1, p. 54 - 63.
[2] Tetrahedron, 2013, vol. 69, # 1, p. 268 - 273.
[3] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 13, p. 2668 - 2674.
  • 4
  • [ 274-09-9 ]
  • [ 141-75-3 ]
  • [ 63740-97-6 ]
YieldReaction ConditionsOperation in experiment
75 g With zinc(II) oxide; zinc(II) chloride In dichloromethane at 0 - 5℃; for 5 h; 122 g of 1,3-benzodioxole and 190 g of dichloromethane were charged into a 1 litre reaction flask and the mixture was cooled to 0°C under stirring. 41 g of Zinc oxide and 7 g of Zinc chloride were added under stirring. Subsequently, 106.5 g of butanoyl chloride was added to the above mixture in 4 hours maintaining the temperature of the reaction medium between 0°C and 5°C under stirring. The reaction medium was stirred for another 1 hour until the acylation reaction was substantially completed. The reaction mass was subjected to aqueous workup to remove Zinc chloride and butanoic acid and the organic layer was separated and distilled to recover 65 g of unreacted 1,3-benzodioxole and 75 g of l-(l,3-benzodioxol-5-yl)-l-butanone with a GC purity of > 99percent. The l-(l,3-benzodioxol-5-yl)-l-butanone was subjected to selective reduction and dehydration as discussed in Example 2 to obtain 66 g of 5-butyl-l,3-benzodioxole with a yield of 115.8percent (wt./wt. on 1,3-benzodioxole consumed) and purity of > 99percent by GC analysis.
References: [1] Patent: WO2018/150230, 2018, A1, . Location in patent: Paragraph 0077; 0078.
  • 5
  • [ 274-09-9 ]
  • [ 91-16-7 ]
  • [ 808-57-1 ]
  • [ 134025-14-2 ]
  • [ 134025-19-7 ]
References: [1] Tetrahedron, 1991, vol. 47, # 4/5, p. 791 - 798.
 

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