Dichloromethane → HCID 178519271, compound

HRID 1657510Notes

Reaction equation

HRID 1657510 reaction equation
[C-:1]1([C:6]([CH2:8][CH2:9][CH2:10][CH2:11][C:12](Cl)=[O:13])=O)[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH-:15]1[CH:19]=[CH:18][CH:17]=[CH:16]1.[Fe+2:20].[Cl-].[Al+3].[Cl-].[Cl-].[CH2:25](Cl)Cl>C1C=CC=CC=1>[C:12]([C:11]1[CH2:10][CH2:9][CH2:8][C:6]=1[C-:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1)(=[O:13])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:15][CH:25]=1.[CH-:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[Fe+2:20]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6451240Aluminum(III) ChlorideHCID 178521142HCID 178521142, compound

Product 1

HCID 178519271HCID 178519271, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Ferrocenoylvaleryl chloride (prepared as above and assumed to be 0.01 mole) was diluted with methylene chloride (10 mls.) and benzene (20 mls.) and the solution was cooled to 0°-5°. Aluminium chloride (2.6g; 0.02 mole) was then added with stirring over 30 minutes. After further stirring at room temperature for 2 hours, ice was added to the reaction mixture. The organic layer was then separated and washed successively with water, aqueous sodium bicarbonate solution, and water, before being dried over sodium sulphate. Evaporation under reduced pressure produced a brown oil from which chromatography on silica gel with toluene/ethyl acetate provided a pure sample of the required compound (0.32 g; 9% yield) mp 135°-7°.

Workup

  1. temperaturethe solution was cooled to 0°-5°
  2. stirringAfter further stirring at room temperature for 2 hours
  3. additionice was added to the reaction mixture
  4. customThe organic layer was then separated
  5. washwashed successively with water, aqueous sodium bicarbonate solution, and water
  6. dry with materialbefore being dried over sodium sulphate
  7. customEvaporation under reduced pressure
  8. customproduced a brown oil from which chromatography on silica gel with toluene/ethyl acetate

Sources & evidence

ORD record
ord-91365668ad334f1d911a1a3567bf16e0
Source dataset
uspto-grants-1976_06
Patent number
US03960911

Reaction notes

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