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

HRID 1470453Notes

Reaction equation

HRID 1470453 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.N1C=CC=CC=1.C(O)(=O)[CH2:17][C:18]([OH:20])=[O:19].Cl>>[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[CH:17][C:18]([OH:20])=[O:19]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 1049PyridineHCID 107222-Methylbenzaldehyde

Product 1

HCID 983063-(2-Methylphenyl)prop-2-enoic acidYield 87%

Procedure

To a stirred solution of o-methylbenzaldehyde (50 g, 417 mmol) in pyridine (2 equiv, 65 mL) was added malonic acid (86.6 g, 834 mmol) and the mixture was refluxed for 4-5 h. The reaction mixture was then poured into ice-water followed by 1N HCl. The white solid precipitated out was filtered, washed with water and concentrated under high vacuum for 3-4 h to get the desired product (57 g, 87%).

Workup

  1. temperaturethe mixture was refluxed for 4-5 h
  2. customThe white solid precipitated out
  3. filtrationwas filtered
  4. washwashed with water
  5. concentrationconcentrated under high vacuum for 3-4 h

Sources & evidence

ORD record
ord-958b298725e04b4ab57ff2eebdb33ccf
Source dataset
uspto-grants-2015_04
Patent number
US09006442B2

Reaction notes

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