1-Bromopropane → 2-Propoxybenzoic acid

HRID 1258980Notes

Reaction equation

[CH2:1](Br)[CH2:2][CH3:3].[C:5]([O:14]CC)(=[O:13])[C:6]1[C:7](=[CH:9][CH:10]=[CH:11][CH:12]=1)[OH:8].C(=O)([O-])[O-].[K+].[K+].C(OC1C=C(C=CC=1)C(O)=O)CC>>[CH2:1]([O:8][C:7]1[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=1[C:5]([OH:14])=[O:13])[CH2:2][CH3:3]

Participants

Reactant 4

HCID 78401-Bromopropane

HCID 8365Ethyl Salicylate

HCID 11430Potassium Carbonate

HCID 5867993-propoxybenzoic acid

Product 1

HCID 5392152-Propoxybenzoic acid

Procedure

The reaction of propyl bromide and ethyl salicylate in the presence of potassium carbonate was performed as described for Compound 24 to give 2-Propoxy-benzoic acid as white powder. 1H-NMR (400 MHz, d6-DMSO): 12.56 (s, COOH); 7.61 (m, 1 arom. H); 7.45 (m, 1 arom. H); 7.07 (m, 1 arom. H); 6.96 (m, 1 arom. H); 3.96 (t, CH3CH2CH2O); 1.71 (m, CH3CH2CH2O); 0.96 (t, CH3CH2CH2O). 13C-NMR (100 MHz, d6-DMSO): 167.49 (—C═O); 157.41; 132.82; 130.51; 121.73; 119.91; 113.35; 69.63; 22.04; 10.39.

Sources & evidence

ORD record: ord-b7a178d97d824b05b589a7da97b18f98
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466199B2

Reaction notes

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