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

HRID 381307Notes

Reaction equation

HRID 381307 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[O:3][CH2:2]1.[Al].[OH2:11].CCCCCC.[C:18]([O:21][CH2:22][CH3:23])(=[O:20])[CH3:19]>ClCCl>[CH2:22]([O:21][C:18](=[O:20])[C:19]([C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH2:2][O:3][C:4]=2[CH:9]=1)=[O:11])[CH3:23]

Participants

7

Reactant 5

HCID 962WaterHCID 8058HexaneHCID 8857Ethyl AcetateHCID 92291,3-BenzodioxoleHCID 5359268Aluminum

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 aluminum thichloride (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-76ffe6d618064c8487fa001f9066f8dd
Source dataset
uspto-grants-2001_10
Patent number
US06306852B1

Reaction notes

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