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

HRID 485842Notes

Reaction equation

HRID 485842 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.C1(C)C=CC=CC=1.C(OO)(=[O:26])C>O>[OH:26][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 1140TolueneHCID 6585Peracetic AcidHCID 3016639Ethyl 2-(4-formylphenoxy)propionate

Product 1

HCID 3017597Propanoic acid, 2-(4-hydroxyphenoxy)-, ethyl esterYield 77.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

While stirring a mixture of 22.5 g of ethyl 2-(4-formylphenoxy)propionate ([α]D25 =+51.5°) and 60 g of toluene at room temperature, 22.8 g of 40% peracetic acid was dropwise added. After stirring at 20° to 30° C. for 2 hours and at 50° C. for 2 hours, 0.2 g of water was added, and the mixture was stirred for 2 hours. After cooling the reaction mixture to room temperature, 40 g of water was added. The aqueous layer was separated. The organic layer was washed with 40 g of water, followed by washing twice with 40 g of a 5% sodium hydrogen carbonate aqueous solution, then with 40 g of a 5% sodium hydrogen sulfite aqueous solution and further with 40 g of water. Then, the reaction mixture was concentrated by distilling off toluene under reduced pressure, and subjected to distillation under reduced pressure, whereby 16.5 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.

Workup

  1. stirringAfter stirring at 20° to 30° C. for 2 hours and at 50° C. for 2 hours
  2. stirringthe mixture was stirred for 2 hours
  3. customThe aqueous layer was separated
  4. washThe organic layer was washed with 40 g of water
  5. washby washing twice with 40 g of a 5% sodium hydrogen carbonate aqueous solution
  6. concentrationThen, the reaction mixture was concentrated
  7. distillationby distilling off toluene under reduced pressure
  8. distillationsubjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-17c524894ba64fb689f706dc73d851be
Source dataset
uspto-grants-1985_08
Patent number
US04537984

Reaction notes

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