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

HRID 485836Notes

Reaction equation

HRID 485836 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]([CH3:19])[C:12]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])=[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]([CH3:19])[C:12]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:13])=[CH:3][CH:4]=1)=[O:7]

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 10340Sodium CarbonateHCID 123534Butyl 2-chloropropanoate

Product 1

HCID 13563056Butyl 2-(4-formylphenoxy)propionateYield 90.4%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

6.1 g of 4-hydroxybenzaldehyde, 9 g of n-butyl 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 washed with dimethylformamide. The solution from the washing was combined with the filtrate, followed by concentration and distillation under reduced pressure, whereby 11.3 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. filtrationThe inorganic salts were filtered off
  3. washwashed with dimethylformamide
  4. concentrationfollowed by concentration and distillation under reduced pressure

Sources & evidence

ORD record
ord-51fa4543198d439cb354b2ae12d270b2
Source dataset
uspto-grants-1985_08
Patent number
US04537984

Reaction notes

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