Butyl bromide → 3-butoxybenzoic acid

HRID 1258981Notes

Reaction equation

[CH2:1](Br)[CH2:2][CH2:3][CH3:4].[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])[CH2:2][CH2:3][CH3:4]

Participants

Reactant 4

HCID 8002Butyl bromide

HCID 11430Potassium Carbonate

HCID 24522Ethyl 3-hydroxybenzoate

HCID 5867993-propoxybenzoic acid

Product 1

HCID 6529553-butoxybenzoic acid

Procedure

The reaction of butyl bromide and ethyl 3-hydroxybenzoate in the presence of potassium carbonate was performed as described for Compound 24 to give 3-butoxy-benzoic acid as white powder. 1H-NMR (400 MHz, d6-DMSO): 12.93 (s, COOH); 7.48 (m, 1 arom. H); 7.40 (m, 2 arom. H); 7.12 (m, 1 arom. H); 3.97 (t, CH3CH2CH2CH2O); 1.69 (m, CH3CH2CH2CH2O); 1.42 (m, CH3CH2CH2CH2O); 0.91 (t, CH3CH2CH2CH2O). 13C-NMR (100 MHz, d6-DMSO): 167.12 (—C═O); 158.63; 132.13; 129.67; 121.40; 119.31; 114.41; 67.30; 30.64; 18.68; 13.65.

Sources & evidence

ORD record: ord-258a5a43fbfb4a00a0f5f5a6f909d81b
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466199B2

Reaction notes

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