Benzyl Alcohol → 2-(Benzyloxymethyl)glutaronitrile

HRID 652292Notes

Reaction equation

HRID 652292 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:11]=[C:12]([CH2:15][CH2:16][C:17]#[N:18])[C:13]#[N:14]>C(OCC)C>[CH2:3]([O:10][CH2:11][CH:12]([CH2:15][CH2:16][C:17]#[N:18])[C:13]#[N:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 740802,4-Dicyano-1-butene

Product 1

HCID 201998762-(Benzyloxymethyl)glutaronitrile

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 50% dispersion of sodium hydride in mineral oil (200 mg.) was added to benzyl alcohol (32.4 g.) and the mixture was stirred until effervescence had ceased. The solution was treated with 2-methyleneglutaronitrile (15.9 g.)and the mixture was kept at room temperature for 24 hours. The reaction mixture was diluted with diethyl ether and the solution was washed three times with water, and then dried and evaporated to dryness to give 2-(benzyloxymethyl)glutaronitrile (32 g.). The crude 2-(benzyloxymethyl)glutaronitrile was reduced with borane-dimethyl sulphide complex in a similar process to that described in Example 1 to give 2-(benzyloxymethyl)pentane-1,5-diamine dihydrochloride, m.p. 159°-161° (after crystallisation from ethanol).

Workup

  1. washthe solution was washed three times with water
  2. customdried
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-9d5310314eff4377a309bba2148a0790
Source dataset
uspto-grants-1987_06
Patent number
US04670592

Reaction notes

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