Sodium hydride → 3-(ethoxymethyl)benzoic acid

HRID 1258996Notes

Reaction equation

HRID 1258996 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7].[H-].[Na+].[CH2:14]([O:18]CC1C=CC(C(O)=O)=CC=1)[CH2:15]C=C>C(O)C>[CH2:14]([O:18][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7])[CH3:15]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2417523-(Chloromethyl)benzoic acidHCID 221369964-But-3-enyloxymethyl-benzoic acid

Product 1

HCID 176060443-(ethoxymethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The reaction of ethanol and 3-Chloromethyl-benzoic acid in the presence of sodium hydride was performed as described for Compound 33 to give 3-ethoxymethyl-benzoic acid as white powder. 1H-NMR (400 MHz, d6-DMSO): 7.89 (m, 1 arom.H); 7.84 (m, 1 arom.H); 7.54 (m, 1 arom.H); 7.46 (m, 1 arom.H); 4.49 (s, OCH2C6H4—); 3.48 (q, J=6.9, CH3CH2); 1.15 (t, J=6.9, CH3CH2). 13C-NMR (100 MHz, d6-DMSO): 167.24 (—C═O); 139.26; 131.67; 130.76; 128.51; 128.23; 128.06; 71.01; 65.14; 15.07.

Sources & evidence

ORD record
ord-b9efb6f7f1bb4b80a53236949d2391a4
Source dataset
uspto-grants-2013_06
Patent number
US08466199B2

Reaction notes

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