1-Bromo-2-methylpropane → 3-isobutoxybenzoic acid

HRID 1258985Notes

Reaction equation

HRID 1258985 reaction equation
[CH2:1](Br)[CH:2]([CH3:4])[CH3:3].[OH:6][C:7]1[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=1)[C:10]([O:12]CC)=[O:11].C(=O)([O-])[O-].[K+].[K+].C(OC1C=C(C=CC=1)C(O)=O)CC>>[CH2:1]([O:6][C:7]1[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=1)[C:10]([OH:12])=[O:11])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 4

HCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 24522Ethyl 3-hydroxybenzoateHCID 5867993-propoxybenzoic acid

Product 1

HCID 8417923-isobutoxybenzoic acid

Procedure

The reaction of isobutyl bromide and ethyl 3-hydroxybenzoate in the presence of potassium carbonate was performed as described for Compound 24 to give 3-isobutoxy-benzoic acid as white powder. 1H-NMR (400 MHz, d6-DMSO): 12.94 (s, COOH); 7.48 (m, 1 arom. H); 7.40 (m, 2 arom. H); 7.12 (m, 1 arom. H); 3.76 (d, J=6.4, (CH3)2CHCH2O); 2.00 (m, (CH3)2CHCH2O); 0.96 (d, J=6.4, (CH3)2CHCH2O). 13C-NMR (100 MHz, d6-DMSO): 167.11 (—C═O); 158.73; 132.12; 129.68; 121.42; 119.35; 114.46; 73.46; 27.66; 18.98 (2 C).

Sources & evidence

ORD record
ord-d3e6bc6c597f4789a76a775989cbc1bb
Source dataset
uspto-grants-2013_06
Patent number
US08466199B2

Reaction notes

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