Hydrochloric Acid → 3,4-Dibenzyloxyphenylacetonitrile

HRID 1655033Notes

Reaction equation

HRID 1655033 reaction equation
[OH:1][C:2]1[C:7](O)=[CH:6][C:5]([CH2:9][C:10]#[N:11])=[CH:4][CH:3]=1.[C:12](=[O:15])([O-])[O-].[K+].[K+].[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>CN(C)C=O.O>[CH2:18]([O:1][C:2]1[C:7]([O:15][CH2:12][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:6][C:5]([CH2:9][C:10]#[N:11])=[CH:4][CH:3]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 109097272-(3,4-Dihydroxyphenyl)acetonitrile

Product 1

HCID 27580313,4-Dibenzyloxyphenylacetonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture consisting of one mole (149 g) of 4,5-dihydroxyphenylacetonitrile prepared in stage 1, two moles of potassium carbon ate (276 g) and 2.2 moles (278,5 g) of benzyl chloride in 745 ml of dimethylformamide is heated to 105°-110° C. for approximately 30 minutes. At the end of the reaction, the reaction mixture is diluted with 2.5 kg of a mixture of ice and water, and is neutralized with hydrochloric ac id while being briskly stirred, The expected product, which has precipitated, is filtered off, washed with water, and is again mixed into a paste with ethanol and then with isopropyl ether.

Workup

  1. temperatureis heated to 105°-110° C. for approximately 30 minutes
  2. customAt the end of the reaction
  3. customThe expected product, which has precipitated
  4. filtrationis filtered off
  5. washwashed with water
  6. additionis again mixed into a paste with ethanol

Sources & evidence

ORD record
ord-08955e05d8bd487ba860380434e72499
Source dataset
uspto-grants-1995_04
Patent number
US05410067

Reaction notes

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