Thionyl Chloride → Benzo(1,3)dioxol-5-yl-acetyl chloride

HRID 1030451Notes

Reaction equation

HRID 1030451 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][C:11]([OH:13])=O)=[CH:4][C:3]=2[O:2]1.S(Cl)([Cl:16])=O>>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][C:11]([Cl:16])=[O:13])=[CH:4][C:3]=2[O:2]1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 76115Benzo-1,3-dioxole-5-acetic acid

Product 1

HCID 2756584Benzo(1,3)dioxol-5-yl-acetyl chloride

Conditions

Temperature
25 °C

Procedure

3,4-methylenedioxyphenyl acetic acid, 50.4 grams, 0.28 mole, was reacted with an excess amount of thionyl chloride, 58 grams, 0.49 moles, in a 250 milliliter round bottom flask at 60° C. for 3 hours. The product mixture resulting was cooled to room temperature, about 25° C., and any excess thionyl chloride was removed with a water aspirator. Pure, about 99.5 percent purity, 3,4-methylenedioxyphenylacetylchloride was isolated as a light reddish oil by vacuum distillation yielding 48.2 grams, an 80 percent yield of product. The boiling point of the aforementioned product was 116° C. at 1.4 millimeters of mercury. IR (neat): 1,795 cm-1 (C=O).

Workup

  1. customThe product mixture resulting
  2. customany excess thionyl chloride was removed with a water

Sources & evidence

ORD record
ord-b3bedf85ae034aff8994d90a9f16d892
Source dataset
uspto-grants-1992_04
Patent number
US05106713

Reaction notes

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