Phenol → 1-(4-Hydroxyphenyl)-3-(4-chlorophenyl)-2-phenyl-2-propen-1-one

HRID 328262Notes

Reaction equation

HRID 328262 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:16])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1.N1CCCCC1.C1(O)C=CC=CC=1>CO.C(O)(=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:16])[C:9]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:22][C:21]2[CH:24]=[CH:25][C:18]([Cl:17])=[CH:19][CH:20]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 77264-ChlorobenzaldehydeHCID 8082PiperidineHCID 75607Benzyl 4-hydroxyphenyl ketone

Product 1

HCID 2677241-(4-Hydroxyphenyl)-3-(4-chlorophenyl)-2-phenyl-2-propen-1-oneYield 34%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

9.4 g (0.0443 mole) of 1-(4-hydroxyphenyl)-2-phenylethanone, 6.23 g (0.0443 mole) of 4-chlorobenzaldehyde and 3.53 g (0.0415 mole) of piperidine in 19.3 ml of methanol was stirred at 35° and then kept overnight. It was worked up as under Example IA to give 14.5 g (83%) of crude product. 14 g (0.0333 mole) of the crude phenol was mixed with 140 ml of glacial acetic acid and refluxed for 4 hours. Work up as under Example IB followed by recrystallization from methanol gave 3.7 g (34%) of pure product, m.p. 179°-181°.

Workup

  1. customto give 14.5 g (83%) of crude product
  2. temperaturerefluxed for 4 hours

Sources & evidence

ORD record
ord-becafc4f52684541a0245eaa0149a493
Source dataset
uspto-grants-1977_04
Patent number
US04016223

Reaction notes

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