1-Bromopropane → p-Propoxybenzoic acid

HRID 1258979Notes

Reaction equation

[CH2:1](Br)[CH2:2][CH3:3].[OH:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12]CC)=[O:11])=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].C(OC1C=C(C=CC=1)C(O)=O)CC>>[CH2:1]([O:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)[CH2:2][CH3:3]

Participants

Reactant 4

HCID 78401-Bromopropane

HCID 8434Ethylparaben

HCID 11430Potassium Carbonate

HCID 5867993-propoxybenzoic acid

Product 1

HCID 138500p-Propoxybenzoic acid

Procedure

The reaction of propyl bromide and ethyl 4-hydroxybenzoate in the presence of potassium carbonate was performed as described for Compound 24 to give 4-Propoxy-benzoic acid as white powder. 1H-NMR (400 MHz, d6-DMSO): 12.58 (s, COOH); 7.86 (d, J=8.8, 2 arom. H); 6.97 (d, J=8.8, 2 arom. H); 3.97 (t, CH3CH2CH2O); 1.72 (m, CH3CH2CH2O); 0.96 (t, CH3CH2CH2O). 13C-NMR (100 MHz, d6-DMSO): 166.99 (—C═O); 162.29; 131.33 (2 arom. C); 122.78; 114.18 (2 arom. C); 69.21; 21.90; 10.30.

Sources & evidence

ORD record: ord-9f29f43d4a24413898ec16197bc56216
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466199B2

Reaction notes

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