Cuminaldehyde → Hydroxy[4-(propan-2-yl)phenyl]acetonitrile

HRID 1080706Notes

Reaction equation

HRID 1080706 reaction equation
[CH:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[C-:12]#[N:13].[Na+].S(=O)(O)[O-].[Na+]>O>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:8]([OH:9])[C:12]#[N:13])=[CH:10][CH:11]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 326CuminaldehydeHCID 8929Sodium CyanideHCID 23665763Sodium Bisulfite

Product 1

HCID 14293609Hydroxy[4-(propan-2-yl)phenyl]acetonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred suspension of 4-isopropylbenzaldehyde (21.4 g) and sodium cyanide (6.9 g) in water (25 ml) at 0° was added saturated sodium bisulfite (40 ml) dropwise over a period of 30 minutes. During the addition about 50 g of ice was also added in small portions. After the addition the mixture was warmed up to room temperature gradually. Resulting waxy 4-isopropylmandelonitrile was separated by decantation and the aqueous layer was extracted with benzene. The benzene extract was evaporated and, the residue was combined with the waxy material. The 4-isopropylmandelonitrile was dissolved in concentrated hydrochloric acid (25 ml) and the mixture was stirred at room temperature overnight. It was then stirred in a 100° oil bath for 3 hours. After cooling was added water to dissolve the solid material and the product was extracted with ethyl ether throughly. The combined extracts were washed with brine, dried (sodium sulfate) and evaporated to give 4-isopropylmandelic acid as an oil (17 g).

Workup

  1. additionwas also added in small portions
  2. additionAfter the addition the mixture

Sources & evidence

ORD record
ord-b4e398d1acb740d581278216d44e0e99
Source dataset
uspto-grants-1996_12
Patent number
US05583147

Reaction notes

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