Water → HCID 14699389, compound

HRID 330306Notes

Reaction equation

HRID 330306 reaction equation
[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7]Cl)[CH2:2][CH3:3].[C-:13]#[N:14].[Na+].O.CCOCC>CS(C)=O>[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7][C:13]#[N:14])[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 8929Sodium CyanideHCID 19869706HCID 19869706, compound

Product 1

HCID 14699389HCID 14699389, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

A 2 liter flask was charged with 367 grams (1.90 moles, 1.0 ec.) of crude 2-propoxybenzyl chloride in 700 ml of DMSO. The reaction is cooled by a water bath and 102 grams of sodium cyanide (2.09 moles, 1.1 eq.) was added and allowed to warm to 50° C. After the exotherm was complete, the reaction was stirred at room temperature overnight then worked up with water, dilute acid and ether. Removal of the solvent was followed by distillation (120°-150° C. at 1 mm) and gave 180 grams (54% Yield) of a light yellow oil.

Workup

  1. temperatureThe reaction is cooled by a water bath
  2. customRemoval of the solvent
  3. distillationwas followed by distillation (120°-150° C. at 1 mm)

Sources & evidence

ORD record
ord-e3c61b1b45b74504a49f239cd66a41d8
Source dataset
uspto-grants-1990_01
Patent number
US04895865

Reaction notes

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