Acetic Acid → 4-((Benzyloxy)carbonyl)benzoic acid

HRID 1424Notes

Reaction equation

HRID 1424 reaction equation
C(O)(=[O:3])C.[CH2:5]([O:12][C:13](=[O:22])[C:14]1[CH:19]=[CH:18][C:17]([CH:20]=[O:21])=[CH:16][CH:15]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>O>[CH2:5]([O:12][C:13]([C:14]1[CH:15]=[CH:16][C:17]([C:20]([OH:3])=[O:21])=[CH:18][CH:19]=1)=[O:22])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 176Acetic Acid2×HCID 11528845Benzyl 4-formylbenzoate

Product 1

HCID 105871574-((Benzyloxy)carbonyl)benzoic acidYield 49%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 50 ml of an acetic acid solution containing 7.34 g (30.5 mmol) of 4-formylbenzoic acid benzyl ester were dropwise added 4.53 g (4.35 mmol) of chromic acid anhydride, 40 ml of acetic acid and 1.3 ml of water with stirring at room temperature for a period of 2 hours. The oxidation of a formyl group was further carried out overnight at room temperature. The reaction mixture was put into water, and the deposited black-green crystal was collected by filtration, followed by drying. The resultant crystal was recrystallized from acetone to obtain 4.08 g of 4-benzyloxycarbonylbenzoic acid as a white needle crystal (isolated yield: 49%).

Workup

  1. waitThe oxidation of a formyl group was further carried out overnight at room temperature
  2. filtrationthe deposited black-green crystal was collected by filtration
  3. customby drying
  4. customThe resultant crystal was recrystallized from acetone
  5. customto obtain

Sources & evidence

ORD record
ord-3241ab6c22d447b498b7ce647cbfc9d9
Source dataset
uspto-grants-1998_03
Patent number
US05725798

Reaction notes

Loading…