Diethyl Ether → Ethyl 4-(2-formylphenoxy)butyrate

HRID 2081306Notes

Reaction equation

HRID 2081306 reaction equation
[CH:1](=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[H-].[Na+].[CH2:12]([O:14][C:15](=[O:20])[CH2:16][CH2:17][CH2:18]Br)[CH3:13].CCOCC>CN(C)C=O>[CH2:12]([O:14][C:15](=[O:20])[CH2:16][CH2:17][CH2:18][O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[CH:1]=[O:9])[CH3:13]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6998SalicylaldehydeHCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 11390709Ethyl 4-(2-formylphenoxy)butyrateYield 47.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 12.2 g of salicylaldehyde in 20 ml of dimethylformamide is instilled into a suspension of 4.36 g of sodium hydride (55% dispersion in mineral oil) in 80 ml of dimethylformamide by stirring and ice cooling within 15 minutes. After 3 hours, a solution of 21.5 g of 4-bromobutyric acid ethyl ester in 16 ml of dimethylformamide is instilled by ice cooling within 15 minutes, and the mixture is stirred for 72 hours at room temperature. The batch is poured on ice/water, shaken with ether, the organic phase is washed briefly with 1 n sodium hydroxide solution, dried with sodium sulfate and concentrated by evaporation. The crude product is distilled at 130°-140° C./0.1 mbar in a bulb tube and 11.2 g of 4-(2-formylphenoxy)-butyric acid ethyl ester is thus obtained as a colorless oil.

Workup

  1. waitAfter 3 hours
  2. stirringthe mixture is stirred for 72 hours at room temperature
  3. additionThe batch is poured on ice/water
  4. washthe organic phase is washed briefly with 1 n sodium hydroxide solution
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated by evaporation
  7. distillationThe crude product is distilled at 130°-140° C./0.1 mbar in a bulb tube

Sources & evidence

ORD record
ord-5735d4daf4854df9bfb4a6ee3f685b6d
Source dataset
uspto-grants-1993_02
Patent number
US05183925

Reaction notes

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