alpha-Ethyl-alpha-methyl-dihydrocinnamic acid → 2-Ethyl-2-methyl-1-indanone

HRID 261528

Reaction equation

HRID 261528 reaction equation
[CH2:1]([C:3]([CH3:14])([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:4]([OH:6])=O)[CH3:2]>O>[CH2:1]([C:3]1([CH3:14])[CH2:7][C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]1=[O:6])[CH3:2]

Participants

3

Reactant 1

HCID 20394459alpha-Ethyl-alpha-methyl-dihydrocinnamic acid

Product 1

HCID 146860942-Ethyl-2-methyl-1-indanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

69 g of α-ethyl-α-methyl-dihydrocinnamic acid are added dropwise at 150°, within 5 minutes, to 700 g of polyphosphoric acid, while stirring. The reaction mixture is stirred at 160° for a further 10 minutes, is cooled to 100° and 100 cc of water are added dropwise. The reaction mixture is then poured on ice, extracted with ether, the ether extract is washed with water and dried over sodium sulphate. The 2-ethyl-2-methyl-1-indanone, obtained after evaporating the solvent, is purified by distillation. B.P. 137°-140° at 20 mm of Hg.

Workup

  1. stirringThe reaction mixture is stirred at 160° for a further 10 minutes
  2. temperatureis cooled to 100°
  3. additionThe reaction mixture is then poured on ice
  4. extractionextracted with ether
  5. extractionthe ether extract
  6. washis washed with water
  7. dry with materialdried over sodium sulphate

Sources & evidence

ORD record
ord-d280e6f49a1b4e39adc6e5d503e9626b
Source dataset
uspto-grants-1979_08
Patent number
US04166131

Linked notes

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