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

HRID 1941457Notes

Reaction equation

HRID 1941457 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 96.6%

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-edd73702ec874183847f3a1b106318a4
Source dataset
uspto-grants-1997_12
Patent number
US05703239

Reaction notes

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