Hydrochloric Acid → beta-(Hydroxymethyl)-beta-phenylpropionitrile

HRID 566266Notes

Reaction equation

HRID 566266 reaction equation
[C:1]([CH:5]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:6][C:7]#[N:8])(OC)=[O:2].[BH4-].[Na+].Cl>C(COC)OC.CCOCC>[OH:2][CH2:1][CH:5]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:6][C:7]#[N:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 18464584Methyl 3-cyano-2-phenylpropanoate

Product 1

HCID 11457849beta-(Hydroxymethyl)-beta-phenylpropionitrile

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

β-(Carbomethoxy)-β-phenylpropionitrile (144 g, 0.76 mol) is dissolved in dimethoxyethane (1500 mL) and NaBH4 (63.5 g, 1.67 mol) is cautiously added. The reaction mixture is stirred for 30 minutes and then heated at reflux for 2 hours. After this time the resulting solution is allowed to cool to ambient temperature and is poured onto ice. The mixture is then treated with 2N HCl (1500 mL) and is subsequently diluted with Et2O (1500 mL). The organic phase is washed with H2O (1×1000 mL), saturated NaCl solution (2×1000 mL), dried over MgSO4 and concentrated in vacuo to yield β-(hydroxymethyl)-β-phenylpropionitrile.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. additionis poured onto ice
  4. washThe organic phase is washed with H2O (1×1000 mL), saturated NaCl solution (2×1000 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-db6e91c6d37f4749aceaab85d0d4d9f5
Source dataset
uspto-grants-2001_01
Patent number
US06174888B1

Reaction notes

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