Dichloromethane → 3-(2H-1,3-Benzodioxol-5-yl)prop-2-enoyl chloride

HRID 2099991Notes

Reaction equation

HRID 2099991 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[CH:11][C:12]([OH:14])=O)=[CH:9][C:4]=2[O:3][CH2:2]1.[Cl:15]CCl>CN(C)C=O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[CH:11][C:12]([Cl:15])=[O:14])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 169173-(1,3-Benzodioxol-5-yl)prop-2-enoic acid

Product 1

HCID 534112793-(2H-1,3-Benzodioxol-5-yl)prop-2-enoyl chlorideYield 98.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Conditions

Temperature
40 °C

Procedure

(Method G2) To a suspension of 3-benzo[1,3]dioxol-5-yl-acrylic acid (1a) (0.38 g, 1.98 mmol) in dichloromethane (8.0 ml) oxalyl chloride (0.62 ml, 7.08 mmol) and one drop of dimethylformamide were added. The reaction mixture was stirred at 40° C. for one hour and concentrated under reduced pressure to give crude title compound (0.41 g, 98%).

Workup

  1. additionwere added
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-db5a81ad783443499a42067e4584b9aa
Source dataset
uspto-grants-2009_08
Patent number
US07569724B2

Reaction notes

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