4-(Bromomethyl)benzoic acid → 4-(Propoxymethyl)benzoic acid

HRID 1258995Notes

Reaction equation

HRID 1258995 reaction equation
BrCC1C=CC(C(O)=O)=CC=1.[H-].[Na+].[CH2:14]([O:18][CH2:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=1)[CH2:15][CH:16]=C>C(O)CC>[CH2:14]([O:18][CH2:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=1)[CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 225994-(Bromomethyl)benzoic acidHCID 24758Sodium hydrideHCID 221369964-But-3-enyloxymethyl-benzoic acid

Product 1

HCID 176060524-(Propoxymethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

The reaction of propanol and 4-Bromomethyl-benzoic acid in the presence of sodium hydride was performed as described for Compound 33 to give 4-propoxymethyl-benzoic acid as white powder. 1H-NMR (400 MHz, d6-DMSO): 7.89 (d, J=8.2, 2 arom.H); 7.40 (d, J=8.2, 2 arom.H); 4.50 (s, OCH2C6H4—); 3.38 (t, CH3CH2CH2O); 1.54 (m, CH3CH2CH2O); 0.87 (t, CH3CH2CH2O).). 13C-NMR (100 MHz, d6-DMSO): 167.24 (—C═O); 143.94; 129.67; 129.30 (2 arom. C); 127.03 (2 arom. C); 71.53; 71.13; 22.43; 10.55.

Sources & evidence

ORD record
ord-d4ce7b3c76ff40d3b590eb75dc388d67
Source dataset
uspto-grants-2013_06
Patent number
US08466199B2

Reaction notes

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