Acetic Acid → 4-(p-Tolyl)-2-butanone

HRID 280324Notes

Reaction equation

HRID 280324 reaction equation
C([C:6](=[CH:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1)[C:7](=[O:9])[CH3:8])(OCC)=O.C(O)(=O)C.Cl>O=[Pt]=O.O>[CH3:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][CH2:6][C:7](=[O:9])[CH3:8])=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 3674893-Carboethoxy-4-(4-methylphenyl)but-3-en-2-one

Product 1

HCID 54639084-(p-Tolyl)-2-butanone

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 962WaterSolvent

Procedure

3-Carboethoxy-4-(4-methylphenyl)but-2-one (20 g), (prepared by hydrogenation over PtO2 at 1 atmosphere of 3-carboethoxy-4-(4-methylphenyl)but-3-en-2-one) was heated under reflux for 3.5 h in a mixture of glacial acetic acid (48 ml), concentrated hydrochloric acid (5.6 ml) and water (30 ml). The solvent was evaporated, the residue dissolved in xylene, washed with water, dried and evaporated. The residue was distilled to give 4-(4-methylphenyl)butan-2-one, 11.0 g, bp 80-90/1 mm).

Workup

  1. temperaturewas heated
  2. customThe solvent was evaporated
  3. dissolutionthe residue dissolved in xylene
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. distillationThe residue was distilled

Sources & evidence

ORD record
ord-6759616b84334d159ace86c71b43a672
Source dataset
uspto-grants-1986_05
Patent number
US04588749

Reaction notes

Loading…