Acetone Cyanohydrin → HCID 14277662, compound

HRID 1196410Notes

Reaction equation

HRID 1196410 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[C:14]1([CH:20]2[CH2:25][C:24](=[O:26])[CH2:23][C:22](=[O:27])[CH2:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C.CC(C)(O)C#N>ClCCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([CH:23]2[C:22](=[O:27])[CH2:21][CH:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:25][C:24]2=[O:26])=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1

Participants

6

Reactant 4

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2×HCID 5689621,3-Cyclohexanedione, 5-phenyl-HCID 108677844-Chloro-2-nitrobenzoyl chloride

Product 1

HCID 14277662HCID 14277662, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-chloro-2-nitrobenzoyl chloride (4.4 g) in dry dichloromethane (5 ml) was added at 5°-10° C. to a stirred solution of 5-phenylcyclohexane-1,3-dione [3.7 g] and triethylamine (2.8 ml) in dry dichloromethane (50 ml), and the mixture was stirred at ambient temperature for 18 hours. Triethylamine (8.4 ml) and acetone cyanohydrin (0.4 ml) were added successively to the solution and the mixture was stirred at ambient temperature for 4 hours. The resulting solution was washed successively with 2N hydrochloric acid (25 ml) and water (3×25 ml), dried over sodium sulphate and evaporated under reduced pressure to give a brown solid which was recrystallised from acetonitrile to give 2-(4-chloro-2-nitrobenzoyl)-5-phenylcyclohexane-1,3-dione (4.2 g), mp 144°-145° C., as a light cream crystalline solid.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 4 hours
  2. washThe resulting solution was washed successively with 2N hydrochloric acid (25 ml) and water (3×25 ml)
  3. dry with materialdried over sodium sulphate
  4. customevaporated under reduced pressure
  5. customto give a brown solid which
  6. customwas recrystallised from acetonitrile

Sources & evidence

ORD record
ord-1e223224f38c490fb35e4e2520ff2541
Source dataset
uspto-grants-1992_05
Patent number
US05114461

Reaction notes

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