Acetone Cyanohydrin → 2,2,6,6-Tetramethyl-4-(4-chloro-2-nitrobenzoyl)-2H-pyran

HRID 1084626Notes

Reaction equation

HRID 1084626 reaction equation
O1CC=CC(=O)C1.C(N(CC)CC)C.CC(C)(O)C#N.[CH3:21][C:22]1([CH3:44])[O:27][C:26]([CH3:29])([CH3:28])[C:25](=O)[CH:24]([C:31](=[O:42])[C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:33]=2[N+:39]([O-:41])=[O:40])[C:23]1=O>C(#N)C.CCOCC>[CH3:21][C:22]1([CH3:44])[CH2:23][C:24]([C:31](=[O:42])[C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:33]=2[N+:39]([O-:41])=[O:40])=[CH:25][C:26]([CH3:29])([CH3:28])[O:27]1

Participants

7

Reactant 4

HCID 6406Acetone CyanohydrinHCID 8471TriethylamineHCID 46725963,6-dihydro-2H-pyran-3-oneHCID 15116760HCID 15116760, compound

Product 1

HCID 867447062,2,6,6-Tetramethyl-4-(4-chloro-2-nitrobenzoyl)-2H-pyran

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

To a mixture of 2,2,6,6.tetramethyl.5.(4.chloro.2.nitrobenzoyloxy)-3,6-dihydro-2H-pyran-3-one (5.97 g, 16.9 mmol) and triethylamine (4,70 ml, 33.8 mmol) in 30 ml of acetonitrile is added acetone cyanohydrin (0.5 ml), and the mixture is stirred at RT for 24 hours. The reaction mixture is diluted with ether and extracted with aqueous 5% K2CO3. The aqueous layer is made acidic with conc. HCl and extracted with ether. The combined organic layers are dried and evaporated to give light yellow crystals, which are purified to yield 2,2,6,6.tetramethyl-4-(4-chloro-2-nitrobenzoyl) -2H-pyran-3,5-(4H,6H)-dione (compound 8, Table A).

Workup

  1. additionTo a mixture of 2,2,6,6
  2. extractionextracted with aqueous 5% K2CO3
  3. extractionextracted with ether
  4. customThe combined organic layers are dried
  5. customevaporated
  6. customto give light yellow crystals, which
  7. customare purified
  8. customto yield 2,2,6,6

Sources & evidence

ORD record
ord-c0a6d5de0ed24d0bb6d290594c605866
Source dataset
uspto-grants-1991_04
Patent number
US05006150

Reaction notes

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