Hydrochloric Acid → 3-(4-Methoxyphenyl)-2-phenylprop-2-enoic acid

HRID 31238

Reaction equation

HRID 31238 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[C:11]1([CH2:17][C:18]([OH:20])=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].Cl>C(OC(=O)C)(=O)C.O.C(N(CC)CC)C>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH:1]=[C:17]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:18]([OH:20])=[O:19])=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 999Phenylacetic AcidHCID 11430Potassium CarbonateHCID 312444-Methoxybenzaldehyde

Product 1

HCID 2366983-(4-Methoxyphenyl)-2-phenylprop-2-enoic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 7918Acetic AnhydrideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
90 °C

Procedure

Triethylamine was added to solution of p-anisaldehyde (10 g) and phenylacetic acid (10 g) in acetic anhydride (25 ml). Reaction mixture was stirred at 90° C. for 8 h. Reaction mixture was cooled and water (600 ml) solution of potassium carbonate (81 g) was added. After addition reaction mixture was heated at 60° C. for an hour. Before neutralising with concentrated hydrochloric acid the reaction mixture was cooled below 10° C. Precipitate was filtered and washed with water. 1H-NMR (400 MHz, d6-DMSO): 12.6 (bs, 1H), 7.67 (s, 1H), 7.4-7.3 (m, 3H), 7.2-7.1 (m, 2H), 7.0-6.9 (m, 2H), 6.8-6.7 (m, 2H), 3.70 (s, 3H). (M)+=254 (100%).

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. temperaturewas cooled
  4. additionAfter addition reaction mixture
  5. temperaturewas heated at 60° C. for an hour
  6. filtrationPrecipitate was filtered
  7. washwashed with water

Sources & evidence

ORD record
ord-eb11651813c84c2689f6df85f5f39bf2
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Linked notes

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