Benzoyl chloride → HCID 19895648, compound

HRID 892534Notes

Reaction equation

HRID 892534 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][C:6]1([CH3:22])[CH2:11][CH:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[C:9]2[CH:18]=[CH:19][CH:20]=[CH:21][C:8]=2[O:7]1.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>[N+](C)([O-])=O.C(OCC)C>[C:23]([C:19]1[CH:20]=[CH:21][C:8]2[O:7][C:6]([CH3:22])([CH3:5])[CH2:11][CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)[C:9]=2[CH:18]=1)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 198956113,4-dihydro-2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran

Product 1

HCID 19895648HCID 19895648, compoundYield 27.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6375NitromethaneSolvent

Procedure

264 mg of aluminum chloride were added to an ice-cooled solution of 237 mg of 3,4-dihydro-2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran in 6 ml of nitromethane. The mixture was stirred for 5 minutes, 349 mg of benzoyl chloride were added and the stirring was continued at 0° C. for 30 minutes and at room temperature for 16 hours. The o reaction mixture was diluted with diethyl ether and washed with sodium hydroxide solution. The organic phase was dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (2:3) for the elution to give 94 mg of 6-benzoyl-3,4-dihydro-2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran.

Workup

  1. waitthe stirring was continued at 0° C. for 30 minutes and at room temperature for 16 hours
  2. customThe o reaction mixture
  3. washwashed with sodium hydroxide solution
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel
  7. washfor the elution

Sources & evidence

ORD record
ord-6f55ea6f9cea40e7bd91acdb6e97b258
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Reaction notes

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