Phenylacetic Acid → 3-(4-tert-Butyl-phenyl)-2-phenyl-acrylic Acid

HRID 2358423Notes

Reaction equation

HRID 2358423 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]([C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12].C(OC(=O)C)(=O)C>Cl>[C:11]([C:15]1[CH:16]=[CH:17][C:18]([CH:19]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]([OH:10])=[O:9])=[CH:21][CH:22]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 999Phenylacetic AcidHCID 7918Acetic AnhydrideHCID 703244-tert-Butylbenzaldehyde

Product 1

HCID 684536973-(4-tert-Butyl-phenyl)-2-phenyl-acrylic AcidYield 73%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Phenyl acetic acid (489 mg, 3.59 mmol) and 4-t-butylbenzaldehyde (573 mmg, 3.53 mmol), TEA (5 ml) and acetic anhydride (5 ml) were added in round flask. A reaction mixture was heated and stirred overnight. The reaction mixture was poured into 5% HCl aqueous solution (30 ml). A aqueous solution was extracted with MC (30 ml×3). A combined organic layer was dried over MgSO4 and then concentrated in vacuo. The crude residue was column-chromatographed (hexane/ethylacetate=4/1) to yield a white solid (382 mg, 73%)

Workup

  1. temperatureA reaction mixture was heated
  2. extractionA aqueous solution was extracted with MC (30 ml×3)
  3. dry with materialA combined organic layer was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was column-chromatographed (hexane/ethylacetate=4/1)

Sources & evidence

ORD record
ord-85b91df4d42f443ab48b2424d855fb04
Source dataset
uspto-grants-2010_07
Patent number
US07763657B2

Reaction notes

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