Potassium Carbonate → 4-Methoxy-3-(2-methyl-allyloxy)benzoic acid

HRID 1258977Notes

Reaction equation

HRID 1258977 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5]([O:7]C)=[O:6].Br[CH2:15][C:16]([CH3:18])=[CH2:17].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH3:13][O:12][C:11]1[CH:10]=[CH:9][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=1[O:1][CH2:17][C:16]([CH3:18])=[CH2:15]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 3577853-Bromo-2-methyl-1-propeneHCID 4056967Methyl 3-hydroxy-4-methoxybenzoate

Product 1

HCID 250567694-Methoxy-3-(2-methyl-allyloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The reaction of methyl 3-hydroxyl-4-methoxybenzoate and 3-Bromo-2-methyl-propene in 2-butanone in the presence of potassium carbonate was performed as described in Example 2 to give 4-Methoxy-3-(2-methyl-allyloxy)-benzoic acid as white powder. 1H-NMR (400 MHz, d6-DMSO): 12.63 (s, —CO2H); 7.56 (d-like, 1 arom. H); 7.43 (m, 1 arom. H); 7.04 (m, 1 arom. H); 5.04, 4.90 (2 s, —C(CH3)═CH2); 4.48 (s, CH2—C(CH3)═CH2); 3.79 (s, OCH3); 1.75 (s, C(CH3)═CH2). 13C-NMR (100 MHz, d6-DMSO): 167.02 (—C═O); 152.90; 147.18; 140.76; 123.39; 122.84; 113.76; 112.33; 111.28; 71.56; 55.75; 19.16.

Sources & evidence

ORD record
ord-73021b0a88f84f2993896107922d444b
Source dataset
uspto-grants-2013_06
Patent number
US08466199B2

Reaction notes

Loading…