Ethanol → HCID 19880013, compound

HRID 1885111Notes

Reaction equation

HRID 1885111 reaction equation
C(O)C.[O-]CC.[Na+].[C:8]([O:16][CH2:17][CH3:18])(=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].[CH2:19]([O:22][CH:23]([CH3:30])[CH2:24]CS([O-])(=O)=O)[CH2:20][CH3:21]>O>[CH2:19]([O:22][CH:23]([CH3:30])[CH2:24][CH:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:8]([O:16][CH2:17][CH3:18])=[O:15])[CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 702EthanolHCID 7761Diethyl MalonateHCID 2723922Sodium ethoxideHCID 19880008HCID 19880008, compound

Product 1

HCID 19880013HCID 19880013, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into 345 ml of ethanol, 43.4 g of 95%-sodium ethoxide was added, and under stirring, 114 g of diethyl malonate was added dropwise at 33°-36° C. in 55 min. After further 30 min. of stirring, 114 g of the above 2-propoxypropylmethane sulfonate was added at 34°-38° C. in 1 hour. The mixture was heated and refluxed at 80°-82° C. for 18 hours. After the completion, the product was poured in cold water and extracted with benzene, followed by washing with water, removed by distillation of benzene, and vacuum distillation to obtain 100 g of ethyl 4-propoxy-2-ethoxycarbonylvalerate (75°-115° C./5 mmHg).

Workup

  1. stirringAfter further 30 min. of stirring
  2. temperatureThe mixture was heated
  3. temperaturerefluxed at 80°-82° C. for 18 hours
  4. extractionextracted with benzene
  5. washby washing with water
  6. customremoved by distillation of benzene, and vacuum distillation

Sources & evidence

ORD record
ord-f8981fa501e3458691d9dbcae1eaed70
Source dataset
uspto-grants-1992_09
Patent number
US05143643

Reaction notes

Loading…