Hydroxyacetonitrile → HCID 53924730, compound

HRID 902995Notes

Reaction equation

HRID 902995 reaction equation
[Br:1][CH:2]([CH3:6])[C:3](Br)=[O:4].[C:7]([CH2:9][OH:10])#[N:8].C(N(CC)CC)C>C(COC)OC>[C:7]([CH2:9][O:10][C:3](=[O:4])[CH:2]([Br:1])[CH3:6])#[N:8]

Participants

5

Reactant 3

HCID 7857HydroxyacetonitrileHCID 8471TriethylamineHCID 79047Propanoyl bromide, 2-bromo-

Product 1

HCID 53924730HCID 53924730, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

215.9 g (1 mole) of α-bromopropionyl bromide are dissolved in 500 ml of dimethoxy ethane and to the resulting solution are slowly added 62.8 g (1.1 moles) of cyanomethanol at 10° C. Then 111.3 g (1.1 moles) of triethylamine are added dropwise at 10°-20° C. The reaction mixture is stirred for 10 minutes at room temperature and filtered over hyflo. The filtrate is concentrated and the residue is distilled in a water jet vacuum, yielding as main fraction 107 g (55.7%) of α-bromopropionic acid cyanomethyl ester with a boiling point of 109° C./17 torr and having the formula ##STR6##

Workup

  1. customat 10° C
  2. filtrationfiltered over hyflo
  3. concentrationThe filtrate is concentrated
  4. distillationthe residue is distilled in a water jet vacuum

Sources & evidence

ORD record
ord-278da22d63d04952a3c2182352035086
Source dataset
uspto-grants-1980_10
Patent number
US04226614

Reaction notes

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