Benzaldehyde → HCID 54210196, compound

HRID 544168Notes

Reaction equation

HRID 544168 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 aqueouse phase was acidified with 2M 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-782d02a6535340ebb89e5bc33580f075
Source dataset
uspto-grants-1984_05
Patent number
US04448787

Reaction notes

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