Sodium Hydroxide → Sodium diethoxyacetate

HRID 1196570Notes

Reaction equation

HRID 1196570 reaction equation
[CH2:1]([O:3][CH:4]([O:10][CH2:11][CH3:12])[C:5]([O:7]CC)=[O:6])[CH3:2].[OH-].[Na+:14]>C(O)C.O>[CH2:1]([O:3][CH:4]([O:10][CH2:11][CH3:12])[C:5]([O-:7])=[O:6])[CH3:2].[Na+:14]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 80169Ethyl diethoxyacetate

Product 1

HCID 23663712Sodium diethoxyacetateYield 96.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl diethoxyacetate (Ex. Fluka) (25 g) was added to sodium hydroxide (5.68 g) in ethanol (60 ml) and water (30 ml). After heating under reflux for 5 hours the solvents were removed at reduced pressure and the residue dried in vacuo to give sodium diethoxyacetate (23.2 g). The salt was then converted to diethoxyacetyl chloride and reacted with benzylamine to give N-benzyl diethoxyacetamide which was cyclised with conc. sulphuric acid according to Fukumi and Hideshi, Heterocycles, 9, 1197 (1978) to give 3-hydroxyisoquinoline.

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 5 hours the solvents
  3. customwere removed at reduced pressure
  4. customthe residue dried in vacuo

Sources & evidence

ORD record
ord-f1b186e741f441908f127846db9a8931
Source dataset
uspto-grants-1992_05
Patent number
US05114940

Reaction notes

Loading…