Tetrahydrofuran → 4-[2-(p-Cyanophenyl)ethyl]cyclohexanecarboxaldehyde

HRID 1731446Notes

Reaction equation

HRID 1731446 reaction equation
C[O:2][CH:3]=[C:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)[CH2:6][CH2:5]1.O1CCCC1>O>[C:16]([C:15]1[CH:18]=[CH:19][C:12]([CH2:11][CH2:10][CH:7]2[CH2:8][CH2:9][CH:4]([CH:3]=[O:2])[CH2:5][CH2:6]2)=[CH:13][CH:14]=1)#[N:17]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 20159862p-[2-(4-Methoxymethylenecyclohexyl)ethyl]benzonitrile

Product 1

HCID 196954904-[2-(p-Cyanophenyl)ethyl]cyclohexanecarboxaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 23.5 of p-[2-(4-methoxymethylenecyclohexyl)ethyl]benzonitrile and 300 ml of tetrahydrofuran/2N hydrochloric acid (vol. 4:1) was boiled at reflux while gassing with nitrogen for 30 minutes. The cooled reaction mixture was poured into 450 ml of water and extracted three times with 300 ml of diethyl ether each time. The organic phases were washed with 200 ml of water, dried over sodium sulphate and concentrated in vacuo at 50° C. There were obtained 21.9 g of 4-[2-(p-cyanophenyl)ethyl]cyclohexanecarboxaldehyde (trans/cis=4:1) as a colourless oil; Rf-value (methylene chloride) 0.3.

Workup

  1. temperatureat reflux
  2. customThe cooled reaction mixture
  3. extractionextracted three times with 300 ml of diethyl ether each time
  4. washThe organic phases were washed with 200 ml of water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo at 50° C

Sources & evidence

ORD record
ord-29528c88e11b45109fa1cb028072ec7e
Source dataset
uspto-grants-1986_11
Patent number
US04621901

Reaction notes

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