4-Hydroxybenzaldehyde → HCID 53811871, compound

HRID 399198Notes

Reaction equation

HRID 399198 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>[CH2:22]([O:21][C:19](=[O:20])[C:18]([C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH:6][C:5]1[CH:8]=[CH:9][C:2]([OH:1])=[CH:3][CH:4]=1)[CH3:23]

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-c0e77119c5ef43cfbafbb114056c695f
Source dataset
uspto-grants-1998_10
Patent number
US05817693

Reaction notes

Loading…