Sulfuric Acid → 3-Acetyl-2,2-diphenylpropionaldehyde

HRID 1657273Notes

Reaction equation

HRID 1657273 reaction equation
[C:1]1([C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH2:10][C:11]#[CH:12])[CH:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)[OH:20]>C(O)(=O)C.O>[C:11]([CH2:10][C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH:8]=[O:9])(=[O:20])[CH3:12]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 107997012,2-Diphenyl-2-(2-propynyl)acetaldehyde

Product 1

HCID 105627693-Acetyl-2,2-diphenylpropionaldehydeYield 103.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent2×

Procedure

A solution of 2,2-diphenyl-2-(2-propynyl)acetaldehyde (83.0 g) in acetic acid (83 ml) was added dropwise to a solution of mercuric acetate (3.1 g) and sulfuric acid (18.3 g) in a mixture of acetic acid (300 ml) and water (75 ml) over a period of 2 hours at room temperature. The reaction mixture was poured into water and extracted with diethyl ether. The extract was washed successively with water and aqueous solution of sodium bicarbonate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of n-hexane and ethyl acetate (5:1) as an eluent to give 3-acetyl-2,2-diphenylpropionaldehyde (48.9 g).

Workup

  1. extractionextracted with diethyl ether
  2. washThe extract was washed successively with water and aqueous solution of sodium bicarbonate
  3. customevaporated in vacuo
  4. customThe residue was purified by column chromatography on silica gel with a mixture of n-hexane and ethyl acetate (5:1) as an eluent

Sources & evidence

ORD record
ord-a427fd25d33a49188dff91c20c7da880
Source dataset
uspto-grants-1993_10
Patent number
US05256824

Reaction notes

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