Potassium Carbonate → 3-[(2-Methylprop-2-en-1-yl)oxy]benzoic acid

HRID 1258975Notes

Reaction equation

HRID 1258975 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].Br[CH2:14][C:15]([CH3:17])=[CH2:16].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH3:16][C:15](=[CH2:14])[CH2:17][O:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24522Ethyl 3-hydroxybenzoateHCID 3577853-Bromo-2-methyl-1-propene

Product 1

HCID 166413153-[(2-Methylprop-2-en-1-yl)oxy]benzoic acid

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The reaction of Ethyl 3-hydroxyl-benzoate and 3-Bromo-2-methyl-propene in 2-butanone in the presence of potassium carbonate was performed as described in Example 2 to give 3-(2-Methyl-allyloxy)-benzoic acid as white powder. 1H-NMR (400 MHz, d6-DMSO): 7.50 (m, 1 arom. H); 7.44 (m, 2 arom. H); 7.19 (m, 1 arom. H); 5.04, 4.96 (2 s, —C(CH3)═CH2); 4.50 (s, CH2—C(CH3)═CH2); 1.75 (s, C(CH3)═CH2). 13C-NMR (100 MHz, d6-DMSO): 166.93 (—C═O); 158.23; 140.62; 132.14; 129.67; 121.67; 119.53; 114.88; 112.33; 70.95; 19.13.

Sources & evidence

ORD record
ord-707fc9b3ec8a486f8425926ddd823e70
Source dataset
uspto-grants-2013_06
Patent number
US08466199B2

Reaction notes

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