Water → HCID 178509798, compound

HRID 1731433Notes

Reaction equation

HRID 1731433 reaction equation
C[O:2][CH:3]=[CH:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.O>O1CCCC1>[C:15]([C:14]1[CH:17]=[CH:18][C:11]([C@H:8]2[CH2:9][CH2:10][C@H:5]([CH2:4][CH:3]=[O:2])[CH2:6][CH2:7]2)=[CH:12][CH:13]=1)#[N:16]

Participants

4

Reactant 2

HCID 962WaterHCID 178495106HCID 178495106, compound

Product 1

HCID 178509798HCID 178509798, compoundYield 103%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 10.1 g of p-[trans-4-(2-methoxyvinyl)cyclohexyl]benzonitrile in 200 ml of tetrahydrofuran/2N hydrochloric acid (vol. 4:1) was heated to reflux for 1 hour. The reaction mixture was subsequently poured into 200 ml of water and extracted three times with 150 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 9.8 g of [trans-4-(p-cyanophenyl)cyclohexyl]acetaldehyde were obtained as light yellowish crystals (purity 98.7%). Recrystallization of a sample from hexane/t-butyl methyl ether (vol. 1:1) gave pure aldehyde with m.p. 43.4° C.

Workup

  1. temperatureto reflux for 1 hour
  2. extractionextracted three times with 150 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-95b95c2561b345d6ad0f4b84709e2ee4
Source dataset
uspto-grants-1986_11
Patent number
US04621901

Reaction notes

Loading…