beta-Phenylisovaleric acid → 3,3-Dimethyl-1-indanone

HRID 439339

Reaction equation

HRID 439339 reaction equation
[CH3:1][C:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:7])[CH2:3][C:4]([OH:6])=O.P(Cl)(Cl)(Cl)(Cl)Cl.[Cl-].[Al+3].[Cl-].[Cl-]>C1C=CC=CC=1>[CH3:7][C:2]1([CH3:1])[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4](=[O:6])[CH2:3]1

Participants

5

Reactant 3

HCID 13890beta-Phenylisovaleric acidHCID 24819Phosphorus pentachlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 3046283,3-Dimethyl-1-indanone

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 3-methyl-3-phenyl butanoic acid (17.1 g, 95.5 mmoles) in benzene (70 mL) was added PCl5 (23.0 g, 0.11 mole, 1.15 eq.) portionwise with cooling. Upon completion of the addition, the reaction mixture was refluxed for 30 minutes and cooled to room temperature. Aluminum chloride (13.1 g, 98.3 mmoles) was added in increments and the reaction was heated at reflux for 30 minutes. The reaction mixture was poured onto ice; the oily layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organics were washed with 5% HCl solution, saturated NaHCO3 solution, saturated NaCl solution and dried over MgSO4. The solvent was evaporated in vacuo and the crude product (14.3 g) was vacuum distilled (b.p.=103° C. @ 2.3 mmHg) to obtain 9.98 g of the title C compound as a colorless oil. MS: (M+H)+ @ 161.

Workup

  1. temperaturewith cooling
  2. additionUpon completion of the addition
  3. temperaturethe reaction mixture was refluxed for 30 minutes
  4. temperaturethe reaction was heated
  5. temperatureat reflux for 30 minutes
  6. additionThe reaction mixture was poured onto ice
  7. customthe oily layer was separated
  8. extractionthe aqueous layer was extracted with ethyl acetate
  9. washThe combined organics were washed with 5% HCl solution, saturated NaHCO3 solution, saturated NaCl solution
  10. dry with materialdried over MgSO4
  11. customThe solvent was evaporated in vacuo
  12. distillationdistilled (b.p.=103° C. @ 2.3 mmHg)
  13. customto obtain 9.98 g of the title C compound as a colorless oil

Sources & evidence

ORD record
ord-3a23513956604f76840f83f7e488ceb3
Source dataset
uspto-grants-1996_05
Patent number
US05514690

Linked notes

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