Acetone Cyanohydrin → HCID 13983073, compound

HRID 868469Notes

Reaction equation

HRID 868469 reaction equation
C(N(CC)CC)C.[N+:8]([C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13](Cl)=[O:14])([O-:10])=[O:9].[CH3:20][C:21]1([CH3:29])[CH2:26][C:25](=[O:27])[C:24](=O)[CH2:23][CH2:22]1.CC(C)([OH:34])C#N>C(Cl)Cl>[N+:8]([C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([CH:24]1[C:23](=[O:34])[CH2:22][C:21]([CH3:20])([CH3:29])[CH2:26][C:25]1=[O:27])=[O:14])([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 6406Acetone CyanohydrinHCID 8471Triethylamine2×HCID 118752-Nitrobenzoyl chlorideHCID 18411288HCID 18411288, compound

Product 1

HCID 13983073HCID 13983073, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (3.4 ml, 25 mmol) was added dropwise to a methylene chloride solution of 2-nitrobenzoyl chloride (3.5 g, 19 mmol) and 5,5-dimethylcyclohexanedione (2.4 g, 19 mmol). After stirring for one hour at room temperature an additional 3 equivalents of triethylamine and 0.4 ml acetone cyanohydrin were added. The solution was stirred for 2.5 hours, then washed with 2N HCl and extracted with 5% potassium carbonate solution. The basic extracts were acidified with 2N HCl and extracted with ether. The ether portion was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under vacuum. The residue was recrytallized from ethyl acetate yielding 2.0 g of the desired compound (m.p. 130°-133° C.) which was identified as such by nuclear magnetic resonance spectroscopy, infrared spectroscopy and mass spectroscopy.

Workup

  1. additionwere added
  2. washwashed with 2N HCl
  3. extractionextracted with 5% potassium carbonate solution
  4. extractionextracted with ether
  5. washThe ether portion was washed with saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-769257409530491b8740a46b2a1adc6d
Source dataset
uspto-grants-1988_10
Patent number
US04780127

Reaction notes

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