Benzaldehyde → HCID 54210196, compound

HRID 1659492Notes

Reaction equation

HRID 1659492 reaction equation
[CH3:1][C:2]1[O:7][C:6]([C:8]([O:10]CC)=[O:9])=[CH:5][C:4](=[O:13])[CH:3]=1.[O-]CC.[Na+].[Na].[CH:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C.O>[O:13]=[C:4]1[CH:3]=[C:2]([CH:1]=[CH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:7][C:6]([C:8]([OH:10])=[O:9])=[CH:5]1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 15578414HCID 15578414, compound

Product 1

HCID 54210196HCID 54210196, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of this ester (3.6 g) in ethanol (100 ml) was added to a solution of sodium ethoxide prepared by dissolving sodium (1.0 g) in ethanol (100 ml). Benzaldehyde (2.45 ml) was added and the stirred mixture was heated at 80°-90° C. for an hour, cooled, diluted with water (800 ml) and washed with ether. The aqueous phase was acidified with 2 M hydrochloric acid and extracted with ethyl acetate. The extract was dried and evaporated and the solid residue was recrystallised from dimethylformamide-water to give the title product (mp 227°-228° C. with decomposition).

Workup

  1. customprepared
  2. temperaturethe stirred mixture was heated at 80°-90° C. for an hour
  3. temperaturecooled
  4. washwashed with ether
  5. extractionextracted with ethyl acetate
  6. customThe extract was dried
  7. customevaporated
  8. customthe solid residue was recrystallised from dimethylformamide-water

Sources & evidence

ORD record
ord-8117049c0b004bd28d882b974703b00f
Source dataset
uspto-grants-1981_12
Patent number
US04304728

Reaction notes

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