Water → 2-Benzyl-2-methyl-5-methoxy-6,7-dichloro-1-indanone

HRID 1287444Notes

Reaction equation

HRID 1287444 reaction equation
CC(C)([O-])C.[K+].[CH3:7][CH:8]1[CH2:16][C:15]2[C:10](=[C:11]([Cl:20])[C:12]([Cl:19])=[C:13]([O:17][CH3:18])[CH:14]=2)[C:9]1=[O:21].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O>C(O)(C)(C)C.C1C=CC=CC=1>[CH2:22]([C:8]1([CH3:7])[CH2:16][C:15]2[C:10](=[C:11]([Cl:20])[C:12]([Cl:19])=[C:13]([O:17][CH3:18])[CH:14]=2)[C:9]1=[O:21])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 123955612-Methyl-5-methoxy-6,7-dichloro-1-indanoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 123955662-Benzyl-2-methyl-5-methoxy-6,7-dichloro-1-indanone

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 6386tert-ButanolSolvent

Procedure

Potassium tert-butoxide (1.68 g., 0.015 mole) in dry tert-butyl alcohol (40ml.) is added to a refluxing solution of 2-methyl-5-methoxy-6,7-dichloro-1-indanone in benzene (50 ml.). After refluxing for 30 minutes, benzyl bromide (1.72 g., 0.01 mole) in benzene (10 ml.) is added dropwise. After refluxing for an additional 30 minutes the mixture is cooled, water (10 ml.) is added and the mixture is evaporated to dryness. The residue is washed with water and taken up in ether. The ether solution is washed with water and a saturated sodium chloride solution, dried over sodium sulfate and evaporated. The syrupy residue of 2-benzyl-2-methyl-5-methoxy-6,7-dichloro-1-indanone (3 g.) is used directly in the next step without purification.

Workup

  1. temperatureAfter refluxing for 30 minutes
  2. temperatureAfter refluxing for an additional 30 minutes the mixture
  3. temperatureis cooled
  4. customthe mixture is evaporated to dryness
  5. washThe residue is washed with water
  6. washThe ether solution is washed with water
  7. dry with materiala saturated sodium chloride solution, dried over sodium sulfate
  8. customevaporated
  9. customThe syrupy residue of 2-benzyl-2-methyl-5-methoxy-6,7-dichloro-1-indanone (3 g.) is used directly in the next step without purification

Sources & evidence

ORD record
ord-b66eeadd60e64e0fbd7e48ce5d672d83
Source dataset
uspto-grants-1976_10
Patent number
US03984465

Reaction notes

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