Acetic Acid → Cyclohexanecarbonitrile, 1-(1-naphthalenyl)-4-oxo-

HRID 1576203Notes

Reaction equation

HRID 1576203 reaction equation
[C:1]([C:3]1([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=2)[CH2:8][CH:7](C(OC)=O)[C:6](=[O:13])[CH2:5][CH2:4]1)#[N:2].C(O)(=O)C.S(=O)(=O)(O)O>O>[C:1]([C:3]1([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=2)[CH2:8][CH2:7][C:6](=[O:13])[CH2:5][CH2:4]1)#[N:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 12230237HCID 12230237, compound

Product 1

HCID 12230240Cyclohexanecarbonitrile, 1-(1-naphthalenyl)-4-oxo-Yield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 16.73 g. (0.055 mole) of methyl 5-cyano-5-(1-naphthyl)-2-oxocyclohexanecarboxylate (prepared in Example 11) in 400 ml. of acetic acid and 200 ml. of 10% sulfuric acid is stirred mechanically for about 44 hours. The mixture is then allowed to cool and diluted with water. This mixture is extracted thoroughly with benzene. The organic layer is successively washed with water, sodium bicarbonate solution and brine and evaporated to dryness. The solid residue is recrystallized from acetone to give 10.3 g. (76% yield) of 4-cyano-4-(1-naphthyl)cyclohexanone, having a melting point of 213° to 215°C.

Workup

  1. additionA mixture of 16.73 g
  2. temperatureto cool
  3. extractionThis mixture is extracted thoroughly with benzene
  4. washThe organic layer is successively washed with water, sodium bicarbonate solution and brine
  5. customevaporated to dryness
  6. customThe solid residue is recrystallized from acetone
  7. customto give 10.3 g

Sources & evidence

ORD record
ord-0c2df48257f54f2ca34ef7dc2613c2a0
Source dataset
uspto-grants-1976_09
Patent number
US03979444

Reaction notes

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