4-Hydroxybenzaldehyde → HCID 53767661, compound

HRID 1164772Notes

Reaction equation

HRID 1164772 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1.Cl[CH:13]([CH3:17])[C:14]([OH:16])=[O:15]>CN(C)C=O.C([O-])(O)=O.[Na+]>[CH:8]([C:7]1[CH:10]=[CH:11][C:4]([O:3][C@H:13]([CH3:17])[C:14]([O:16][CH2:10][CH2:11][CH2:4][CH2:5][CH2:6][CH3:7])=[O:15])=[CH:5][CH:6]=1)=[O:9]

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 117342-Chloropropionic acidHCID 24758Sodium hydride

Product 1

HCID 53767661HCID 53767661, compoundYield 27.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
110 °C

Procedure

Sodium hydride (0.4 mole) was suspended in dimethyl formamide (20 ml). 4-Hydroxybenzaldehyde (0.2 mole) in DMF (50 ml) was added. After the effervesence had subsided, 2-chloropropanoic acid (0.22 mole) was added dropwise. During the addition the reaction temperature rose to 70° C. The mixture was stirred overnight at 110° C. Upon cooling the mixture was diluted with saturated NaHCO3 solution and extracted with ethyl acetate (3×100 ml). The aqueous phase was then acidified with concentrated HCl solution and extracted with ethyl acetate. After washing the second organic extract with water and evaporation, a brown oil was obtained. Crystallisation from hot chloroform and hexane gave a brown solid (7.6 g). The mother liquors were evaporated to dryness to yield a brown solid (17.3 g) used without further purification. (Total yield 64%). 'H-NMR spectroscopy showed these products to be greater than 90% pure (m.p. 114°-8° C.).

Workup

  1. additionDuring the addition the reaction temperature
  2. customrose to 70° C
  3. temperatureUpon cooling the mixture
  4. extractionextracted with ethyl acetate (3×100 ml)
  5. extractionextracted with ethyl acetate
  6. washAfter washing the second
  7. extractionorganic extract with water and evaporation
  8. customa brown oil was obtained
  9. customCrystallisation from hot chloroform and hexane

Sources & evidence

ORD record
ord-c1e6fe155b0f4f8e97fcffc5c0392381
Source dataset
uspto-grants-1990_03
Patent number
US04906402

Reaction notes

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