Ethyl Glycolate → Ethoxycarbonylmethyl 3-phenylpropanoate

HRID 68009

Reaction equation

HRID 68009 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 nD30 1.4900 and d430 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-0bc7aad0b1304a1690b89b3371a5b570
Source dataset
uspto-grants-1982_08
Patent number
US04347378

Linked notes

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