Hydrochloric Acid → 3-(2-Methylphenyl)prop-2-enoic acid

HRID 973921Notes

Reaction equation

HRID 973921 reaction equation
Cl[C:2]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])(C(C)=O)[C:3]([O:5]CC)=[O:4].[OH-].[Na+].Cl>C1(C)C=CC=CC=1>[CH3:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH:11]=[CH:2][C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19987140Ethyl 2-chloro-2-(o-methylbenzyl)-acetoacetate

Product 1

HCID 983063-(2-Methylphenyl)prop-2-enoic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

292 g (1.08 moles) of ethyl 2-chloro-2-(o-methylbenzyl)-acetoacetate were added dropwise to 4.85 moles of 25% strength aqueous NaOH solution in the course of 1 hour. The refluxed mixture was then stirred for a further 6 hours. The reaction solution was reacted twice by shaking with toluene and then acidified with semiconcentrated hydrochloric acid, and the precipitate which had separated out was filtered off under suction. It was rinsed with water and toluene and dried in a drying oven. 157 g (90% of the theoretical yield) of o-methylcinnamic acid of melting point 176° to 177° C. were obtained.

Workup

  1. customThe reaction solution was reacted twice
  2. customthe precipitate which had separated out
  3. filtrationwas filtered off under suction
  4. washIt was rinsed with water and toluene
  5. customdried in a drying oven

Sources & evidence

ORD record
ord-db85ee3fad21413194b1b6d166d91c3f
Source dataset
uspto-grants-1991_11
Patent number
US05066640

Reaction notes

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