Water → HCID 178509796, compound

HRID 247671Notes

Reaction equation

HRID 247671 reaction equation
C[O:2][CH:3]=[CH:4][CH2:5][CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1.O>O1CCCC1>[C:17]([C:16]1[CH:19]=[CH:20][C:13]([C@H:10]2[CH2:11][CH2:12][C@H:7]([CH2:6][CH2:5][CH2:4][CH:3]=[O:2])[CH2:8][CH2:9]2)=[CH:14][CH:15]=1)#[N:18]

Participants

4

Reactant 2

HCID 962WaterHCID 178494963HCID 178494963, compound

Product 1

HCID 178509796HCID 178509796, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.95 g of p-[trans-4-(4-methoxy-3-butenyl)cyclohexyl]benzonitrile in 100 ml of tetrahydrofuran/2N hydrochloric acid (vol. 4:1) was heated to reflux for 15 minutes. The reaction 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 twice with 100 ml of water each time, dried over magnesium sulphate and concentrated, whereby 2.6 g (93%) of 4-[trans-4-(p-cyanophenyl)cyclohexyl]butyraldehyde were obtained as a slightly yellowish oil; Rf-value (toluene/ethyl acetate vol. 95:5) 0.23.

Workup

  1. temperatureto reflux for 15 minutes
  2. extractionextracted three times with 100 ml of diethyl ether each time
  3. washThe organic phases were washed twice with 100 ml of water each time
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-44bde04dfaaa4b75874bcd42b61fca1a
Source dataset
uspto-grants-1987_11
Patent number
US04709030

Reaction notes

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