Allyl bromide → 4-Methoxy-2-(prop-2-en-1-yloxy)benzoic acid

HRID 1258965Notes

Reaction equation

HRID 1258965 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[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]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5])[CH:15]=[CH2:14]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 79523Methyl 4-methoxysalicylate

Product 1

HCID 215068784-Methoxy-2-(prop-2-en-1-yloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The reaction of methyl 2-hydroxy-4-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-4-methoxy-benzoic acid as white powder. 1H-NMR (400 MHz, d6-DMSO): 12.18 (s, —CO2H); 7.70 (m, 1 arom. H); 6.58 (m, 2 arom. H); 6.01 (m, —CH═CH2); 5.51, 5.24 (2 d-like, CH═CH2); 4.62 (d-like, CH2—CH═CH2); 3.81 (s, OCH3). 13C-NMR (100 MHz, d6-DMSO): 166.45 (C═O); 163.45; 159.40; 133.25; 133.22; 116.91; 112.98; 105.37; 100.01; 68.63; 55.45.

Sources & evidence

ORD record
ord-0cb38a9346ae486a95249c0ad0f5a709
Source dataset
uspto-grants-2013_06
Patent number
US08466199B2

Reaction notes

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