Acetic Acid → 4-Benzoylbenzoic acid

HRID 1935613Notes

Reaction equation

HRID 1935613 reaction equation
C[C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12]C=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[CH3:16][C:17]([OH:19])=[O:18].OS(O)(=O)=O>O>[C:6]([C:8]1[CH:13]=[CH:12][C:16]([C:17]([OH:19])=[O:18])=[CH:10][CH:9]=1)(=[O:7])[C:5]1[CH:14]=[CH:15][CH:2]=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 86524-Methylbenzophenone

Product 1

HCID 691474-Benzoylbenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 4-methylbenzophenone (25 g, 0.127 mole) with HOAc (130 mL) was added successively CrO3 (35 g), H2O (80 mL) and conc. H2SO4 (25 mL). The mixture was heated for 3 hours at 100±5° C. and then quenched by adding ice water (500 mL) to yield a crude 4-benzoylbenzoic acid solid which was dissolved in a 10% KOH solution and filtered. The filtrate was acidified with diluted HCl to pH 2.0 and precipitate by subjected to ice bath. The precipitate was collected to obtain 21.3 g 4-benzoylbenzoic acid in a yield of 74.1%.

Workup

  1. customquenched
  2. additionby adding ice water (500 mL)

Sources & evidence

ORD record
ord-a4b576ffed1248adbf041a6b5e96a58c
Source dataset
uspto-grants-2002_05
Patent number
US06387942B2

Reaction notes

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