2-Butene, 1-bromo- → Methyl 3-(2-buten-1-yloxy)-5-methoxybenzoate

HRID 1284023Notes

Reaction equation

HRID 1284023 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[C:6]([OH:12])[CH:5]=1.[CH2:14](Br)[CH:15]=[CH:16][CH3:17]>>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[C:6]([O:12][CH2:14][CH:15]=[CH:16][CH3:17])[CH:5]=1

Participants

3

Reactant 2

HCID 1224142-Butene, 1-bromo-HCID 13941268Methyl 3-hydroxy-5-methoxybenzoate

Product 1

HCID 54212692Methyl 3-(2-buten-1-yloxy)-5-methoxybenzoate

Procedure

3,5-Dimethoxy-4-(1-methyl) propyl-benzoyl chloride. Starting from 3-hydroxy-5-methoxy-benzoic acid methyl ester by reaction with 2-butenylbromide, 3-(2-butenyloxy)-5-methoxy-benzoic acid methyl ester is obtained. B.p. 156°-58°C/0.4 mmHg. By operating as described under C) the 3,5-dimethoxy-4-(3-methylpropen-3-yl)-benzoic acid is obtained. M.p. 140°-41°C (from diethyl ether/light petroleum). This compound is hydrogenated as under D) to give 3,5-dimethoxy-4-(1-methyl)propyl-benzoic acid, m.p. 125°-26°C (from diethyl ether/light petroleum). This compound is allowed to react with thionyl chloride, thus obtaining the title compound. M.p. 47°-48°C (from diethyl ether upon cooling).

Sources & evidence

ORD record
ord-f0c2cd2811f142e4a629161e9a4bf4d1
Source dataset
uspto-grants-1976_08
Patent number
US03978065

Reaction notes

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