Piperidine → 4-[4-(Hexyloxy)phenyl]-3-(4-methoxyphenyl)-2-butanone

HRID 846262

Reaction equation

HRID 846262 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=[O:12])[CH3:11])=[CH:5][CH:4]=1.[CH2:13]([O:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].N1CCCCC1>C1(C)C=CC=CC=1>[CH2:13]([O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][CH:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:10](=[O:12])[CH3:11])=[CH:22][CH:21]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 312311-(p-Methoxyphenyl)-2-propanoneHCID 79816p-(Hexyloxy)benzaldehyde

Product 1

HCID 198851474-[4-(Hexyloxy)phenyl]-3-(4-methoxyphenyl)-2-butanoneYield 46%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

49.2 g of 3-(4-methoxyphenyl)-2-propanone and 61.8 g of 4-hexyloxybenzaldehyde were added to 100 ml of toluene containing 4 ml of piperidine. The resultant mixture was heated at reflux temperature overnight after which the solvent was removed in vacuo to afford the desired subtitled intermediate (46% yield), b.p. 230°-235° C.

Workup

  1. temperatureat reflux temperature overnight after which the solvent
  2. customwas removed in vacuo

Sources & evidence

ORD record
ord-19e7f61cde12489b985d8cc75dfc7d32
Source dataset
uspto-grants-1992_08
Patent number
US05135955

Linked notes

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