Sodium Cyanide → 2-(3-(Hydroxymethyl)oxetan-3-yl)acetonitrile

HRID 375696

Reaction equation

HRID 375696 reaction equation
Br[CH2:2][C:3]1([CH2:7][OH:8])[CH2:6][O:5][CH2:4]1.[C-:9]#[N:10].[Na+]>C(O)C>[OH:8][CH2:7][C:3]1([CH2:2][C:9]#[N:10])[CH2:6][O:5][CH2:4]1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 529264[3-(Bromomethyl)oxetan-3-yl]methanol

Product 1

HCID 110079092-(3-(Hydroxymethyl)oxetan-3-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 42 g (0.23 mol) of [3-(bromomethyl)oxetan-3-yl] methanol (produced according to Example 1) in 420 ml of ethanol was refluxed with 13 g (0.265 mol) of sodium cyanide for 18 hours. After cooling to room temperature, the precipitated sodium bromide was filtered off and the filtrate concentrated by evaporation. The residue was distilled at 0.4 torr. The yield of product as a colorless oil was 16 g (54 percent). The boiling point of the product was 107° C./0.4 torr. Other data concerning the product was:

Workup

  1. filtrationthe precipitated sodium bromide was filtered off
  2. concentrationthe filtrate concentrated by evaporation
  3. distillationThe residue was distilled at 0.4 torr
  4. customwas 107° C.

Sources & evidence

ORD record
ord-3fcf3ec291cc42e19566979fd5a4612d
Source dataset
uspto-grants-1996_01
Patent number
US05486622

Linked notes

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