4-Hydroxybenzaldehyde → HCID 53811871, compound

HRID 862914Notes

Reaction equation

HRID 862914 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.N1CCCCC1>CCO.C(O)(=O)C>[C:10]([C:18](=[CH:6][C:5]1[CH:8]=[CH:9][C:2]([OH:1])=[CH:3][CH:4]=1)[C:19]([O:21][CH2:22][CH3:23])=[O:20])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 7170Ethyl benzoylacetateHCID 8082Piperidine

Product 1

HCID 53811871HCID 53811871, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent2×

Procedure

To a solution of 4-hydroxybenzaldehyde (31.7 g, 0.26 mol) and ethyl benzoylacetate (45.5 ml, 0.26 mol) in EtOH (45 ml) under an argon atmosphere was added piperidine (2.6 ml, 0.026 mol) and acetic acid (3 drops). After stirring at room temperature overnight, the resulting solid mixture was treated with hot EtOH (700 ml), and then allowed to cool. The crystals which formed were collected by filtration to afford the title compound (61.0 g, 79%).

Workup

  1. temperatureto cool
  2. customThe crystals which formed
  3. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-13e49c76305c45c78f0ce159a563c709
Source dataset
uspto-grants-1998_02
Patent number
US05719182

Reaction notes

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