4-Hydroxybenzaldehyde → Ethyl 2-(4-formylphenoxy)propionate

HRID 485837Notes

Reaction equation

HRID 485837 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C:10]([O:15][CH2:16][CH3:17])(=[O:14])[CH:11]([CH3:13])O.S([O-])(=O)(=O)C.C(=O)([O-])[O-].[K+].[K+]>[I-].[K+].CN(C)C=O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][CH:11]([CH3:13])[C:10]([O:15][CH2:16][CH3:17])=[O:14])=[CH:3][CH:4]=1)=[O:7]

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 17913560(-)-Ethyl lactate mesylate

Product 1

HCID 3016639Ethyl 2-(4-formylphenoxy)propionateYield 80.2%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

6.1 g of 4-hydroxybenzaldehyde, 10.8 g of (-)-ethyl lactate-mesylate ([α]D25 =-54°, optical purity: 96%), 4 g of potassium carbonate, 0.2 g of potassium iodide and 100 g of dimethyl formamide, were mixed, and the reaction was stirred at 100° C. for 5 hours and then cooled to room temperature. The reaction mixture was subjected to liquid separation with an addition of toluene and water. The organic layer was washed twice with water, and after distilling off toluene, subjected to distillation under reduced pressure, whereby 8.9 g of (+)-ethyl 2-(4-formylphenoxy)propionate was obtained as a colorless transparent liquid. The boiling point was from 130° to 140° C./1 mmHg.

Workup

  1. temperaturecooled to room temperature
  2. customThe reaction mixture was subjected to liquid separation with an addition of toluene and water
  3. washThe organic layer was washed twice with water
  4. distillationafter distilling off toluene
  5. distillationsubjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-301c42a058524dd8ae8f7ae3d3355a2e
Source dataset
uspto-grants-1985_08
Patent number
US04537984

Reaction notes

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