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

HRID 485835Notes

Reaction equation

HRID 485835 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Cl[CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13].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]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:3][CH:4]=1)=[O:7]

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 10340Sodium CarbonateHCID 10807Ethyl 2-chloropropionate

Product 1

HCID 3016639Ethyl 2-(4-formylphenoxy)propionateYield 92.8%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

6.1 g of 4-hydroxybenzaldehyde, 7 g of ethyl α-chloropropionate, 4 g of sodium carbonate, 0.2 g of potassium iodide and 20 g of dimethyl formamide, were mixed, and the mixture was stirred at 100° C. for 5 hours and then cooled to room temperature. The inorganic salts were filtered off, and the residue was washed with dimethylformamide. The solution from the washing was combined with the filtrate, followed by concentration and distillation under reduced pressure, whereby 10.3 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. filtrationThe inorganic salts were filtered off
  3. washthe residue was washed with dimethylformamide
  4. concentrationfollowed by concentration and distillation under reduced pressure

Sources & evidence

ORD record
ord-3c1a025e3f51494e8df058558a2fa720
Source dataset
uspto-grants-1985_08
Patent number
US04537984

Reaction notes

Loading…