Hydrochloric Acid → HCID 178509804, compound

HRID 653357Notes

Reaction equation

HRID 653357 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][CH:12]([CH:15]=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].[BH4-].[Na+].Cl>[OH-].[K+]>[OH:16][CH2:15][C@H:12]1[CH2:13][CH2:14][C@H:9]([C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=2)[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 117698294-(4-Formylcyclohexyl)benzonitrile

Product 1

HCID 178509804HCID 178509804, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

4.0 g of 4-(p-cyanophenyl)cyclohexanecarboxaldehyde (prepared according to Example 1) were dissolved in 50 ml of 0.1N methanolic potassium hydroxide solution while gassing with argon in a sulphonation flask provided with a thermometer and the solution was treated portionwise at 0° C. within 20 minutes with 711 mg of sodium borohydride. The mixture was stirred at 0° C. for a further 10 minutes, neutralized with 1N hydrochloric acid and concentrated on a rotary evaporator. The residue was taken up in 200 ml of water and extracted three times with 100 ml of methylene chloride each time. The organic phases were washed twice with 100 ml of water each time, dried over magnesium sulphate and concentrated. A single crystallization of the residue (4.2 g) from 90 ml of ethyl acetate/petroleum ether (vol. 1:2) at 0° C. gave 3.27 g (77%) of p-[trans-4-(hydroxymethyl)cyclohexyl]benzonitrile as colourless crystals of melting point 109.8° C.; purity 99.4%.

Workup

  1. customwhile gassing with argon in a sulphonation flask
  2. customprovided with a thermometer
  3. concentrationconcentrated on a rotary evaporator
  4. extractionextracted three times with 100 ml of methylene chloride each time
  5. washThe organic phases were washed twice with 100 ml of water each time
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated
  8. customA single crystallization of the residue (4.2 g) from 90 ml of ethyl acetate/petroleum ether (vol. 1:2) at 0° C.

Sources & evidence

ORD record
ord-70cc274dfac24689b4089720236ef97f
Source dataset
uspto-grants-1987_06
Patent number
US04676604

Reaction notes

Loading…