Water → HCID 178509797, compound

HRID 1731434Notes

Reaction equation

HRID 1731434 reaction equation
C[O:2][CH:3]=[CH:4][CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1.O>O1CCCC1>[C:16]([C:15]1[CH:18]=[CH:19][C:12]([C@H:9]2[CH2:10][CH2:11][C@H:6]([CH2:5][CH2:4][CH:3]=[O:2])[CH2:7][CH2:8]2)=[CH:13][CH:14]=1)#[N:17]

Participants

4

Reactant 2

HCID 962WaterHCID 178495003HCID 178495003, compound

Product 1

HCID 178509797HCID 178509797, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.04 g of p-[trans-4-(3-methoxy-2-propenyl)cyclohexyl]benzonitrile in 100 ml of tetrahydrofuran/2N hydrochloric acid (vol. 4:1) was heated to reflux for 1 hour. 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 1.9 g (99%) of 3-[trans-4-(p-cyanophenyl)cyclohexyl]propionaldehyde were obtained as colourless crystals; Rf-value (ethyl acetate/petroleum ether vol. 10:90) 0.15.

Workup

  1. temperatureto reflux for 1 hour
  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-34293fab57a2438ab61334a80c3b2369
Source dataset
uspto-grants-1986_11
Patent number
US04621901

Reaction notes

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