Allyl bromide → 3-Allyloxy-benzoic acid

HRID 1258960Notes

Reaction equation

HRID 1258960 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7]CC)=[O:6].[CH2:13](Br)[CH:14]=[CH2:15].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:15]([O:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([OH:7])=[O:6])[CH:14]=[CH2:13]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 24522Ethyl 3-hydroxybenzoate

Product 1

HCID 64838843-Allyloxy-benzoic acid

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The reaction of ethyl 3-hydroxybenzoate and allyl bromide in 2-butanone in the presence of potassium carbonate was performed as described in Example 2 to give 3-Allyloxy-benzoic acid as white powder. 1H-NMR (400 MHz, d6-DMSO): 12.97 (s, —CO2H); 7.47 (d-like, 1 arom. H); 7.40 (m, 2 arom. H); 7.18 (m, 1 arom. H); 5.99 (m, —CH═CH2); 5.37, 5.23 (2 d-like, CH═CH2); 4.03 (d-like, CH2—CH_CH2). 13C-NMR (100 MHz, d6-DMSO): 167.08 (C═O); 158.12; 133.44; 132.27; 129.67; 121.66; 119.47; 117.47; 114.78; 68.27.

Sources & evidence

ORD record
ord-fd7f734c470c44688f9b2c2b5b191e99
Source dataset
uspto-grants-2013_06
Patent number
US08466199B2

Reaction notes

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