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

HRID 485838Notes

Reaction equation

HRID 485838 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][CH2:17][CH2:18][CH3:19])(=[O:14])[CH:11]([CH3:13])O.S([O-])(=O)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>[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][CH2:17][CH2:18][CH3:19])=[O:14])=[CH:3][CH:4]=1)=[O:7]

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 10340Sodium CarbonateHCID 131714319(-)-Butyl lactate mesylate

Product 1

HCID 13563056Butyl 2-(4-formylphenoxy)propionateYield 82.4%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

6.1 g of 4-hydroxybenzaldehyde, 12.3 g of (-)-butyl lactate-mesylate ([α]D25 =-49.1°), 4 g of sodium carbonate, 0.2 g of potassium iodide and 100 g of dimethyl formamide, were mixed, and the mixture 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 10.3 g of (+)-butyl 2-(4-formylphenoxy)propionate was obtained as a colorless transparent liquid. The boiling point was from 135° to 140° C./0.1 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-8973343850244d618f7a7d9ddfac1889
Source dataset
uspto-grants-1985_08
Patent number
US04537984

Reaction notes

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