Tetrahydrofuran → 4-(4-Formylcyclohexyl)benzonitrile

HRID 1111498

Reaction equation

HRID 1111498 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 purificarion: 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 The organic phases
  4. washwere washed once with 100 ml of water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated There

Sources & evidence

ORD record
ord-b1a963f121af4e11a3e10c9c616588d7
Source dataset
uspto-grants-1990_12
Patent number
US04980486

Linked notes

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