Allyl bromide → HCID 25056773, compound

HRID 1258964Notes

Reaction equation

HRID 1258964 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[CH2:14](Br)[CH:15]=[CH2:16].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:16]([O:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:3]=1[C:4]([OH:6])=[O:5])[CH:15]=[CH2:14]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 4072341Methyl 2-hydroxy-5-methoxybenzoate

Product 1

HCID 25056773HCID 25056773, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The reaction of methyl 2-hydroxy-5-methoxy-benzoate and allyl bromide in 2-butanone in the presence of potassium carbonate was performed as described in Example 2 to give 2-Allyloxy-5-methoxy-benzoic acid as white powder. 1H-NMR (400 MHz, d6-DMSO): 12.65 (br, —CO2H); 7.11 (m, 1 arom.H); 7.00 (m, 2 arom.H); 5.95 (m, —CH═CH2); 5.39, 5.17 (2 d-like, CH═CH2); 4.49 (d-like, CH2—CH═CH2); 3.68 (s, OCH3). 13C-NMR (100 MHz, d6-DMSO): 167.06 (C═O); 152.69; 150.99; 133.70; 122.54; 118.27; 116.84; 115.76; 115.08; 69.50; 55.49.

Sources & evidence

ORD record
ord-86a04ece7ce64ff88d461b81949191a9
Source dataset
uspto-grants-2013_06
Patent number
US08466199B2

Reaction notes

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