1-Bromo-2-methylpropane → 4-Isobutoxybenzoic acid

HRID 1258984Notes

Reaction equation

[CH2:1](Br)[CH:2]([CH3:4])[CH3:3].[OH:6][C:7]1[CH:17]=[CH:16][C:10]([C:11]([O:13]CC)=[O:12])=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].C(OC1C=C(C=CC=1)C(O)=O)CC>>[CH2:1]([O:6][C:7]1[CH:17]=[CH:16][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1)[CH:2]([CH3:4])[CH3:3]

Participants

Reactant 4

HCID 65551-Bromo-2-methylpropane

HCID 8434Ethylparaben

HCID 11430Potassium Carbonate

HCID 5867993-propoxybenzoic acid

Product 1

HCID 4606894-Isobutoxybenzoic acid

Procedure

The reaction of isobutyl bromide and ethyl 4-hydroxybenzoate in the presence of potassium carbonate was performed as described for Compound 24 to give 4-isobutoxy-benzoic acid as white powder. 1H-NMR (400 MHz, d6-DMSO): 12.56 (s, COOH); 7.85 (d, J=8.8, 2 arom. H); 6.98 (d, J=8.8, 2 atom. H); 3.80 (d, J=6.4, (CH3)2CHCH2O); 2.01 (m, (CH3)2CHCH2O); 0.96 (d, J=6.4, (CH3)2CHCH2O). 13C-NMR (100 MHz, d6-DMSO): 166.97 (—C═O); 162.35; 131.32 (2 arom. C); 122.78; 114.22 (2 arom. C); 73.89; 27.60; 18.94.

Sources & evidence

ORD record: ord-b11864160b284ff3bceedd91dc482589
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466199B2

Reaction notes

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