Benzene → HCID 21516774, compound

HRID 1659178Notes

Reaction equation

HRID 1659178 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([CH:9]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([O:21][CH3:22])=[C:14]([Cl:20])[C:15]=2[Cl:19])[C:10]1=[O:23])[CH3:8].[CH:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[Cl-].C1([I+]C2C=CC=CC=2)C=CC=CC=1>C(O)(C)(C)C.O>[CH2:7]([C:9]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([O:21][CH3:22])=[C:14]([Cl:20])[C:15]=2[Cl:19])[C:10]1=[O:23])[CH3:8]

Participants

7

Reactant 4

HCID 241BenzeneHCID 73870Diphenyliodonium chlorideHCID 21516783HCID 21516783, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21516774HCID 21516774, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent2×

Procedure

Potassium tert-butoxide (8.4 g.) dissolved in tert-butanol (300 ml.) is added to a refluxing solution of 2-ethyl-4,5-dichloro-6-methoxyindan-1,3-dione (1.3 g) in tert-butanol (400 ml.)-benzene (200 ml.) and refluxing is continued for 15 min., then diphenyliodonium chloride (19.0 g.) is added and refluxing is continued for an additional 2 hours. The reaction mixture is cooled to 25°, 300 ml. water added, and the mixture concentrated to dryness in vacuo to give 2-ethyl-2-phenyl-4,5-dichloro-6-methoxyindan-1,3-dione.

Workup

  1. temperaturerefluxing
  2. temperaturerefluxing
  3. waitis continued for an additional 2 hours
  4. temperatureThe reaction mixture is cooled to 25°
  5. concentrationthe mixture concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-d9754c17be8e4f25ba3580e4e4d5670a
Source dataset
uspto-grants-1976_06
Patent number
US03966966

Reaction notes

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