Ethyl Glycolate → Ethoxycarbonylmethyl 3-phenylpropanoate

HRID 358103

Reaction equation

HRID 358103 reaction equation
[C:1](Cl)(=[O:10])[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[CH2:13][OH:14]>N1C=CC=CC=1>[C:1]([O:14][CH2:13][C:12]([O:16][CH2:17][CH3:18])=[O:15])(=[O:10])[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 12184Ethyl GlycolateHCID 64801Benzenepropanoyl chloride

Product 1

HCID 321703Ethoxycarbonylmethyl 3-phenylpropanoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

33.7 g (0.2 mole) of hydrocinnamoyl chloride was added to a stirred solution of 18 g (0.2 mole) of ethyl glycolate in 20 ml of pyridine. The precipitated pyridine hydrochloride was filtered, washed with benzene, and discarded. The benzene solution of carboethoxymethyl hydrocinnamate was water washed, dried over sodium sulfate, and the solvent stripped off using a rotary evaporator. The yield of product was essentially quantitative. Its structure was established by infrared and nuclear magnetic resonance spectroscopy. It had n30D 1.4900 and d304 1.0919.

Workup

  1. filtrationThe precipitated pyridine hydrochloride was filtered
  2. washwashed with benzene
  3. washwashed
  4. dry with materialdried over sodium sulfate
  5. customa rotary evaporator

Sources & evidence

ORD record
ord-a380bc8c55ea4569a6187fa61adaa645
Source dataset
uspto-grants-1984_08
Patent number
US04464392

Linked notes

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