Boron tribromide → Ethyl 3,4-dihydroxy-γ-oxobenzenebutanoate

HRID 1579289Notes

Reaction equation

HRID 1579289 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[O:18]C)[C:6]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7].B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[OH:18])[C:6]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 249925Ethyl 4-(3,4-dimethoxyphenyl)-4-oxobutanoate

Product 1

HCID 11253386Ethyl 3,4-dihydroxy-γ-oxobenzenebutanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 3-(3,4-dimethoxybenzoyl)propionate was demethylated with boron tribromide in dichloromethane at -80°C to give ethyl 3-(3,4-dihydroxybenzoyl)propionate, m.p. 116°-117°C.

Sources & evidence

ORD record
ord-3e898f75e2d64b99ba982e5264afafda
Source dataset
uspto-grants-1976_01
Patent number
US03931177

Reaction notes

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