Hydrochloric Acid → 3-(4-ethylphenyl)prop-2-enoic Acid

HRID 1956147Notes

Reaction equation

HRID 1956147 reaction equation
[CH2:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1)[CH3:2].C(O)(=O)[CH2:12][C:13]([OH:15])=[O:14].N1CCCC1.Cl>N1C=CC=CC=1>[CH2:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[CH:12][C:13]([OH:15])=[O:14])=[CH:5][CH:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 208614-EthylbenzaldehydeHCID 31268Pyrrolidine

Product 1

HCID 14827523-(4-ethylphenyl)prop-2-enoic AcidYield 96.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4-ethylbenzaldehyde (26.0 g, 0.2 mol), malonic acid (41.6 g, 0.4 mol), pyrrolidine (3 ml), and pyridine (80 ml) was heated in an 85° C. oil bath for 16 hr. The reaction mixture was poured over crushed ice (800 ml), and then made acidic with 12N HCl (100 ml). The white precipitate was filtered, suspended in 1N HCl, and filtered again. The white precipitate was washed with water and air dried to give 4-ethyl cinnamic acid (34.0 g, 96.6).

Workup

  1. additionThe reaction mixture was poured
  2. filtrationThe white precipitate was filtered
  3. filtrationfiltered again
  4. washThe white precipitate was washed with water and air
  5. customdried

Sources & evidence

ORD record
ord-6528794c5a394030a92f2c88f6573a8a
Source dataset
uspto-grants-1998_07
Patent number
US05780470

Reaction notes

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