Benzene → 3-Methyl-indan-1-one

HRID 512082

Reaction equation

HRID 512082 reaction equation
[C:1](O)(=[O:5])/[CH:2]=[CH:3]/[CH3:4].[Al+3].[Cl-].[Cl-].[Cl-].[CH:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH3:4][CH:3]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:1](=[O:5])[CH2:2]1

Participants

4

Reactant 3

HCID 241BenzeneHCID 637090Crotonic AcidHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2595603-Methyl-indan-1-one

Procedure

A solution of crotonic acid (20 g, 0.232 moles) in benzene (147 ml) was added AlCl3 (93 g, 0.748 moles) and the mixture was refluxed for 7 hours. Completion of the reaction was monitored by HPLC & GC. Excess benzene was distilled off and the reaction mixture was poured slowly into ice cold HCl. The organic compound was extracted with ethylacetate. The organic phase was washed thoroughly with water, dried, and evaporated under vacuum. The resultant oil was purified by high vacuum distillation (90-94° C. at ˜2 mm) giving 25 g (74%) of 99.2% pure 3-methyl-indan-1-one.

Workup

  1. temperaturethe mixture was refluxed for 7 hours
  2. distillationExcess benzene was distilled off
  3. additionthe reaction mixture was poured slowly into ice cold HCl
  4. extractionThe organic compound was extracted with ethylacetate
  5. washThe organic phase was washed thoroughly with water
  6. customdried
  7. customevaporated under vacuum
  8. distillationThe resultant oil was purified by high vacuum distillation (90-94° C. at ˜2 mm)

Sources & evidence

ORD record
ord-63677571ca124c49822a0b918e7b4e56
Source dataset
uspto-grants-2015_08
Patent number
US09102597B2

Linked notes

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