Thionyl Chloride → HCID 19899194, compound

HRID 981803Notes

Reaction equation

HRID 981803 reaction equation
[CH3:1][C:2]([CH3:15])([CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][C:4]([OH:6])=O.S(Cl)(Cl)=O.[Cl-].[Cl-].[Cl-].[Al+3]>C(Cl)Cl>[CH3:15][C:2]1([CH3:1])[CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:4](=[O:6])[CH2:3]1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) ChlorideHCID 22620527HCID 22620527, compound

Product 1

HCID 19899194HCID 19899194, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

82 g of 3,3-dimethyl-5-phenylvaleric acid are treated with 57 ml of thionyl chloride and heated to reflux for half an hour. Thereafter, the excess reagent is evaporated, finally under a high vacuum for 1.5 hours. The acid chloride prepared, dissolved in 300 ml of methylene chloride, is added within 3.5 hours under an argon atmosphere to 79 g of aluminum trichloride in 650 ml of methylene chloride. Thereafter, the reaction mixture is stirred for an additional 10 minutes and poured on to ice. The organic phase is washed with water dried and evaporated. After chromatography on silica gel with petroleum ether (low-boiling)/ethyl acetate (98:2), there are obtained 62 g of 6,7,8,9-tetrahydro-7,7-dimethyl-5H-benzocycloheptene-5-one.

Workup

  1. temperatureheated
  2. temperatureto reflux for half an hour
  3. customThereafter, the excess reagent is evaporated, finally under a high vacuum for 1.5 hours
  4. customThe acid chloride prepared
  5. additionpoured on to ice
  6. washThe organic phase is washed with water
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-4ad0ef43df0e49ba99166d0257801506
Source dataset
uspto-grants-1991_02
Patent number
US04992574

Reaction notes

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