Water → Ethyl (2H-1,3-benzodioxol-5-yl)(oxo)acetate

HRID 1934596Notes

Reaction equation

HRID 1934596 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[O:3][CH2:2]1.[Cl-].[Cl-].[Cl-].[Al+3].[OH2:14].CCCCCC.[C:21]([O:24][CH2:25][CH3:26])(=[O:23])[CH3:22]>ClCCl>[CH2:25]([O:24][C:21](=[O:23])[C:22]([C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH2:2][O:3][C:4]=2[CH:9]=1)=[O:14])[CH3:26]

Participants

7

Reactant 5

HCID 962WaterHCID 8058HexaneHCID 8857Ethyl AcetateHCID 92291,3-BenzodioxoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2758872Ethyl (2H-1,3-benzodioxol-5-yl)(oxo)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of ethyl oxalyl chloride (50 ml, 0.45 mmol) and 1,3-benzodioxole (50 g, 0.41 mmol) in dichloromethane (40 ml) was added dropwise to a stirred slurry of aluminium trichloride (71 g, 0.53 mmol) in dichloromethane (500 ml) at 0° C. under a nitrogen atmosphere. After 2 hours the mixture was poured into iced water and the organic layer was washed with further volumes of water (3×500 ml), saturated sodium bicarbonate solution (500 ml) and brine (500 ml). The organic layer was dried (magnesium sulphate) and concentrated to give an orange oil. Flash column chromatography (90% hexane, 10% ethyl acetate) gave 30 g of the subtitle compound as a pale yellow oil.

Workup

  1. washthe organic layer was washed with further volumes of water (3×500 ml), saturated sodium bicarbonate solution (500 ml) and brine (500 ml)
  2. dry with materialThe organic layer was dried (magnesium sulphate)
  3. concentrationconcentrated
  4. customto give an orange oil

Sources & evidence

ORD record
ord-b8622bb014b94875ab4d55870c6b58ec
Source dataset
uspto-grants-2002_05
Patent number
US06384070B2

Reaction notes

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