Tetrahydrofuran → 4-(4-Formylcyclohexyl)benzonitrile

HRID 653354

Reaction equation

HRID 653354 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>O>[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 2

HCID 8028TetrahydrofuranHCID 19739357p-[4-(Methoxymethylene)cyclohexyl]benzonitrile

Product 1

HCID 117698294-(4-Formylcyclohexyl)benzonitrileYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.2 g of p-[4-(methoxymethylene)cyclohexyl]benzonitrile and 100 ml of tetrahydrofuran/2N hydrochloric acid (vol. 4:1) was heated to reflux for 30 minutes in a round flask. The mixture was subsequently poured into 100 ml of water and extracted three times with 100 ml of diethyl ether each time. The organic phases were washed once with 100 ml of water, dried over magnesium sulphate and concentrated. There were obtained 3.9 g (100%) of 4-(p-cyanophenyl)cyclohexanecarboxaldehyde as a colourless oil which was used in the next step without further purification: trans/cis ratio about 3:1, Rf-value (ethyl acetate/petroleum vol. 3:7) 0.41. By recrystallization from hexane there could be obtained pure trans-4-(p-cyanophenyl)cyclohexanecarboxaldehyde; m.p. 57.1° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 30 minutes in a round flask
  3. extractionextracted three times with 100 ml of diethyl ether each time
  4. washThe organic phases were washed once with 100 ml of water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-eddb7b5a620f411aad9f8f9596132082
Source dataset
uspto-grants-1987_06
Patent number
US04676604

Linked notes

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