Benzoate → Benzoic acid, 2-ethoxy-4-methyl-, ethyl ester

HRID 1719673Notes

Reaction equation

HRID 1719673 reaction equation
[C:1]([O-])(=O)[C:2]1C=CC=CC=1.[OH:10][C:11]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:14].C([O-])([O-])=O.[K+].[K+].S(OCC)(O[CH2:31][CH3:32])(=O)=O>CC(C)=O>[CH2:1]([O:10][C:11]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:12]=1[C:13]([O:15][CH2:31][CH3:32])=[O:14])[CH3:2]

Participants

6

Reactant 4

HCID 242BenzoateHCID 57882-Hydroxy-p-toluic acidHCID 6163Diethyl SulfateHCID 11430Potassium Carbonate

Product 1

HCID 11816602Benzoic acid, 2-ethoxy-4-methyl-, ethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The ethyl 2-ethoxy-4-(2-<2-chloro-pyridine-3-carboxamido>ethyl)benzoate used as the starting material was prepared in the following manner: 2-hydroxy-4-methylbenzoic acid was reacted with K2CO3 and diethyl sulfate in acetone to give ethyl 2-ethoxy-4-methylbenzoate (boiling point at 1 mm=107°-108° C.), which was hydrolyzed to give the corresponding carboxylic acid (melting point 72°-74° C., from acetone). Subsequent bromination provided the 4-bromomethyl compound (melting point 98°-100° C.), which gave the 4-cyanomethyl compound (melting point 114°-117° C.) with sodium cyanide. Ethyl 2-ethoxy-4-(2-aminoethyl)benzoate hydrochloride was obtained by catalytic hydrogenation with Raney nickel and reaction with ethanolic hydrochloric acid, and this was reacted with 2-chloronicotinic acid, methyl chloroformate and triethylamine to give ethyl 2-ethoxy-4-(2-<2-chloro-pyridine-3-carboxamido>ethyl)benzoate (melting point 83°-85° C. after column purification).

Workup

  1. customwas prepared in the following manner

Sources & evidence

ORD record
ord-98ad32acb3e042b9bbe85bdbbc3bac9f
Source dataset
uspto-grants-1985_09
Patent number
US04542127

Reaction notes

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