Potassium Carbonate → 1005163-13-2

HRID 1258962Notes

Reaction equation

HRID 1258962 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].[CH3:13][C:14]([CH3:18])=[CH:15][CH2:16]Br.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH3:13][C:14]([CH3:18])=[CH:15][CH2:16][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 700922-Butene, 1-bromo-3-methyl-

Product 1

HCID 250567741005163-13-2

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The reaction of ethyl 3-hydroxybenzoate and 3,3-dimethylallyl bromide in 2-butanone in the presence of potassium carbonate was performed as described in Example 2 to give 3-(3-Methyl-but-2-enyloxy)-benzoic acid as white powder. 1H-NMR (400 MHz, d6-DMSO): 12.97 (br, —CO2H); 7.48 (m, 1 arom.H); 7.42 (m, 1 arom.H); 7.41 (m, 1 arom.H); 7.15 (m, 1 arom.H); 5.40 (m, CH═C(CH3)2); 4.54 (d-like, CH2CH═C(CH3)2); 1.69, 1.63 (2s, CH═C(CH3)2). 13C-NMR (100 MHz, d6-DMSO): 167.16 (C═O); 158.38; 137.32; 132.24; 129.59; 121.43; 119.68; 119.48; 114.67; 64.46; 25.40; 18.00.

Sources & evidence

ORD record
ord-4f67108dcec74fb3a1cd6b01d10ee6b6
Source dataset
uspto-grants-2013_06
Patent number
US08466199B2

Reaction notes

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