Hydrochloric Acid → 3-[3-(4-Methoxyphenyl)propyl]glutaric acid

HRID 67207

Reaction equation

HRID 67207 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH:12]=O)=[CH:5][CH:4]=1.C([CH2:16][C:17]([OH:19])=[O:18])#N.[OH-:20].[Na+].Cl.[CH2:23]([CH2:26][O:27]C)OC>O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH2:11][CH:12]([CH2:23][C:26]([OH:27])=[O:20])[CH2:16][C:17]([OH:19])=[O:18])=[CH:7][CH:8]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 80711,2-DimethoxyethaneHCID 9740Cyanoacetic acidHCID 14798Sodium HydroxideHCID 104875554-(4-Methoxyphenyl)butanal

Product 1

HCID 205288273-[3-(4-Methoxyphenyl)propyl]glutaric acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4(4-Methoxyphenyl)butyraldehyde (5.34 g) is reacted with cyanoacetic acid (5.15 g) and sodium hydroxide (2.74 g) in a mixture of glyme (50 ml) and water (60 ml). The mixture is treated with hydrochloric acid and processed as described in Example 2A to afford the title compound (2.1 g) which on crystallization from ethyl acetate-chloroform-hexane had a melting point of 71°-73° C.

Sources & evidence

ORD record
ord-10b05713b21542bd86cd938be251207c
Source dataset
uspto-grants-1982_08
Patent number
US04345096

Linked notes

Loading…