Tetrahydrofuran → 4-(4-Formylcyclohexyl)benzonitrile

HRID 1285050Notes

Reaction equation

HRID 1285050 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 ether 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-8242dcd0d0b7413289ed8df1bdfa0ce4
Source dataset
uspto-grants-1986_01
Patent number
US04565425

Reaction notes

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