Allyl bromide → Methyl 3-(Allyloxy)-5-methoxybenzoate

HRID 1581021Notes

Reaction equation

HRID 1581021 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]=[CH2:16].C(=O)([O-])[O-].[K+].[K+]>>[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][CH2:16][CH:15]=[CH2:14])[CH:5]=1

Participants

4

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 13941268Methyl 3-hydroxy-5-methoxybenzoate

Product 1

HCID 53682818Methyl 3-(Allyloxy)-5-methoxybenzoate

Procedure

3-Hydroxy-5-methoxybenzoic acid methyl ester is reacted with allyl bromide in the presence of potassium carbonate to give 3-allyloxy-5-methoxybenzoic acid methyl ester. B.p. 128°-30°C/0.4 mmHg. The ester is hydrolized to the corresponding acid with 20% potassium hydroxide in aqueous ethanol. The acid (m.p. 85°-7°C) when heated for 2 hours at 230°C undergoes Claisen rearrangement and cyclization to the title compound which melts at 195°-7°C.

Sources & evidence

ORD record
ord-a9efad00ab2947f5b932dbc893150888
Source dataset
uspto-grants-1976_01
Patent number
US03935236

Reaction notes

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