Dichloromethane → Propanoic acid, 2-(4-hydroxyphenoxy)-, ethyl ester

HRID 485844Notes

Reaction equation

HRID 485844 reaction equation
C([C:3]1[CH:16]=[CH:15][C:6]([O:7][CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][CH:4]=1)=O.C(Cl)Cl.ClC1C=CC=C(C(OO)=[O:28])C=1>O>[OH:28][C:3]1[CH:16]=[CH:15][C:6]([O:7][CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 3016639Ethyl 2-(4-formylphenoxy)propionate

Product 1

HCID 3017597Propanoic acid, 2-(4-hydroxyphenoxy)-, ethyl esterYield 52.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.2 g of (+)-ethyl 2-(4-formylphenoxy)propionate ([α]D25 =+51.3° optical purity: 93%), 10 ml of methylene chloride and 2.6 g of m-chloroperbenzoic acid, was reacted for 2 hours under reflux, and after an addition of 0.5 g of water, further refluxed for 1 hour. After cooling, the reaction mixture was washed twice with 20 g of a 5% sodium hydrogen carbonate aqueous solution, then with 10 g of a 5% sodium hydrogen sulfite aqueous solution and further with 10 g of water. Then, the reaction mixture was concentrated by distilling off methylene chloride and then subjected to distillation under reduced pressure, whereby 1.1 g of ethyl 2-(4-hydroxyphenoxy)propionate was obtained as a colorless transparent liquid. The boiling point was from 130° to 140° C./1 mmHg. [α]D25 =+40.6°, optical punity: 90%

Workup

  1. customwas reacted for 2 hours
  2. temperatureunder reflux
  3. temperaturefurther refluxed for 1 hour
  4. temperatureAfter cooling
  5. washthe reaction mixture was washed twice with 20 g of a 5% sodium hydrogen carbonate aqueous solution
  6. concentrationThen, the reaction mixture was concentrated
  7. distillationby distilling off methylene chloride
  8. distillationsubjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-4909f5171cc247088b935b76a6db923e
Source dataset
uspto-grants-1985_08
Patent number
US04537984

Reaction notes

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