p-[4-(Methoxymethylene)cyclohexyl]benzonitrile → 4-(4-Formylcyclohexyl)benzonitrile

HRID 1249307Notes

Reaction equation

HRID 1249307 reaction equation
C[O:2][CH:3]=[C:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1>O1CCCC1.Cl>[C:14]([C:13]1[CH:16]=[CH:17][C:10]([CH:7]2[CH2:8][CH2:9][CH:4]([CH:3]=[O:2])[CH2:5][CH2:6]2)=[CH:11][CH:12]=1)#[N:15]

Participants

4

Reactant 1

HCID 19739357p-[4-(Methoxymethylene)cyclohexyl]benzonitrile

Product 1

HCID 117698294-(4-Formylcyclohexyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

The resulting oil (11.0 g) of p-[4-(methoxymethylidene)cyclohexyl]benzonitrile was heated to boiling for 1 hour in a mixture of 200 ml of tetrahydrofuran and 50 ml of 2N hydrochloric acid. The mixture was subsequently poured on to 500 ml of ice/water and extracted three times with 200 ml of diethyl ether each time. The organic phases were washed neutral with water, dried over sodium sulphate and concentrated, thereby obtaining 10.0 g of colourless and in part solid 4-(p-cyanophenyl)cyclohexanecarboxaldehyde (cis/trans ratio about 1:3).

Workup

  1. extractionextracted three times with 200 ml of diethyl ether each time
  2. washThe organic phases were washed neutral with water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0fe35845c7b44829822e67c15cec2364
Source dataset
uspto-grants-1986_12
Patent number
US04630896

Reaction notes

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