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

HRID 27374
Notes
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Reaction equation

HRID 27374 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
ParticipantsProcedureSources & evidenceReaction notes

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-343353e5d2dc4a2a924c7fd14af0282b
Source dataset
uspto-grants-1980_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04221725

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes