Benzaldehyde → HCID 54351713, compound

HRID 2309574Notes

Reaction equation

HRID 2309574 reaction equation
C[C:2]1[C:3]([OH:16])=[C:4]([CH2:12][C:13]([OH:15])=[O:14])[CH:5]=[C:6]([C:8](=[O:11])[CH2:9][CH3:10])[CH:7]=1.C(=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH2:25](O)C.Cl>O.CCOCC>[CH3:25][C:9](=[CH:10][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:8]([C:6]1[CH:7]=[CH:2][C:3]([OH:16])=[C:4]([CH2:12][C:13]([OH:15])=[O:14])[CH:5]=1)=[O:11]

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 702EthanolHCID 53819351HCID 53819351, compound

Product 1

HCID 54351713HCID 54351713, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

11 g of methyl 5-propanoyl-2-hydroxy-benzeneacetic acid, 10,6 g of benzaldehyde, 150 ml of ethanol and 50 ml of ether saturated with hydrogen chloride are refluxed for 5 days. The solution is poured on to water and extracted with ethyl acetate. The ethyl acetate is evaporated and the residue is hydrolyzed in sodium hydroxide solution. The pH is adjusted to 7 and the solution is washed with ethyl acetate. The aqueous phase is acidified with hydrochloric acid and extracted with ethyl acetate. The ethyl acetate is evaporated, the residue is leached with dichloroethane and recrystallized from 2-butanone/1,2-dichloroethane. NMR spectrum and elemental analysis data are consistent with the structure of the title compound. Melting point 192° C.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe ethyl acetate is evaporated
  3. washthe solution is washed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. customThe ethyl acetate is evaporated
  6. customrecrystallized from 2-butanone/1,2-dichloroethane

Sources & evidence

ORD record
ord-21c79554a55c4c88bfd2b07d94bb1480
Source dataset
uspto-grants-1987_09
Patent number
US04695648

Reaction notes

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