Acetone Cyanohydrin → HCID 14793311, compound

HRID 1649619Notes

Reaction equation

HRID 1649619 reaction equation
ClC1C=CC(C([O:8][C:9]2[CH:18]3[CH:13]([CH2:14][CH2:15][CH2:16][CH2:17]3)[CH2:12][C:11](=[O:19])[CH:10]=2)=O)=C([N+]([O-])=O)C=1.[Cl:25][C:26]1[CH:45]=[CH:44][C:29]([C:30](OC2CC3C(CCCC3)C(=O)C=2)=[O:31])=[C:28]([N+:46]([O-:48])=[O:47])[CH:27]=1.C(N(CC)CC)C.CC(C)(O)C#N>C(#N)C>[Cl:25][C:26]1[CH:45]=[CH:44][C:29]([C:30]([CH:10]2[C:11](=[O:19])[CH2:12][CH:13]3[CH:18]([CH2:17][CH2:16][CH2:15][CH2:14]3)[C:9]2=[O:8])=[O:31])=[C:28]([N+:46]([O-:48])=[O:47])[CH:27]=1

Participants

6

Reactant 4

HCID 6406Acetone CyanohydrinHCID 8471TriethylamineHCID 14793310HCID 14793310, compoundHCID 14793312HCID 14793312, compound

Product 1

HCID 14793311HCID 14793311, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 1-(4-chloro-2-nitrobenzoyloxy)-4a,5,6,7, 8,8a-hexahydro-3(4H)-naphthalenone and 3-(4-chloro-2-nitrobenzoyloxy)-4a,5,6,7,8,8a-hexahydro-l(4H)-naphthalenone (17.75 g, 50.6 mmol) in 100 ml of acetonitrile is added triethylamine (14.1 ml). Acetone cyanohydrin (2.5 ml) is added and the mixture is stirred overnight at RT. The solvent is removed under vacuum and the residue is dissolved in ether. The solution is washed with 2N HCl, separated and the organic layer is dried. The crude product is purified by chromatography to give 2-(4-chloro-2-nitrobenzoyl)-4a,5,6,7, 8,8a-hexahydro-1,3-(2H,4H)-naphthalenedione, a pure white crystalline solid (compound 1), m.p. 112°.

Workup

  1. customThe solvent is removed under vacuum
  2. dissolutionthe residue is dissolved in ether
  3. washThe solution is washed with 2N HCl
  4. customseparated
  5. customthe organic layer is dried
  6. customThe crude product is purified by chromatography

Sources & evidence

ORD record
ord-0bcefdd8e0d945538a8ba82b43685f85
Source dataset
uspto-grants-1990_05
Patent number
US04921526

Reaction notes

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