Butyl bromide → 4-Butoxybenzoic acid

HRID 1258982Notes

Reaction equation

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

Participants

Reactant 4

HCID 8002Butyl bromide

HCID 8434Ethylparaben

HCID 11430Potassium Carbonate

HCID 5867993-propoxybenzoic acid

Product 1

HCID 729714-Butoxybenzoic acid

Procedure

The reaction of butyl bromide and ethyl 4-hydroxybenzoate in the presence of potassium carbonate was performed as described for Compound 24 to give 4-butoxy-benzoic acid as white powder. 1H-NMR (400 MHz, d6-DMSO): 12.57 (s, COOH); 7.85 (d, J=8.8, 2 arom. H); 6.98 (d, J=8.8, 2 arom. H); 4.02 (t, CH3CH2CH2CH2O); 1.69 (m, CH3CH2CH2CH2O); 1.43 (m, CH3CH2CH2CH2O); 0.92 (t, CH3CH2CH2CH2O). 13C-NMR (100 MHz, d6-DMSO): 166.99 (—C═O); 162.29; 131.32 (2 arom. C); 122.77; 114.17 (2 arom. C); 67.45; 30.58; 18.66; 13.63.

Sources & evidence

ORD record: ord-414f31f6c0854c17818caeee181eb578
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466199B2

Reaction notes

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