3-Hydroxy-4-(1-oxo-2-phenylpropyl)phenol → HCID 19991239, compound

HRID 345745Notes

Reaction equation

HRID 345745 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([OH:18])[CH:5]=[CH:6][C:7]=1[C:8](=[O:17])[CH:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:10].C(O[C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH:42]=[CH:41][C:37]([C:38](Cl)=[O:39])=[CH:36][CH:35]=2)=[CH:30][CH:29]=1)CCCCCCC>C(Cl)(Cl)Cl.CCCCCC>[CH2:4]([C:28]1[CH:29]=[CH:30][C:31]([C:34]2[CH:35]=[CH:36][C:37]([C:38]([O:18][C:4]3[CH:5]=[CH:6][C:7]([C:8](=[O:17])[CH:9]([C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)[CH3:10])=[C:2]([OH:1])[CH:3]=3)=[O:39])=[CH:41][CH:42]=2)=[CH:32][CH:33]=1)[CH2:3][CH2:2][CH2:7][CH2:8][CH2:9][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 107765403-Hydroxy-4-(1-oxo-2-phenylpropyl)phenolHCID 110784734-(4-Octyloxyphenyl)benzoyl chloride

Product 1

HCID 19991239HCID 19991239, compound

Reagents, catalysts & solvents 1

HCID 21585165Chloroform hexaneSolvent

Procedure

600 mg (2.5 millimols) of the thus obtained 3-hydroxy-4-(1-oxo-2-phenylpropyl)phenol was reacted with 830 mg (2.4 millimols) of 4-(4'-octyloxyphenyl)benzoic acid chloride, similar to the procedure as described in Preparation Example 2, to obtain 960 mg of a crude product. The crude product was refined through silica gel column chromatography while using a mixed solvent of chloroform/hexane (50/50) as the eluent. The refined product was recrystallized from a mixed solvent of chloroform/ethanol (20/80) to obtain 153 mg of 3-hydroxy-4-(1-oxo-2-phenylpropyl)phenyl 4-(4'-octylphenyl)benzoate.

Workup

  1. customas described in Preparation Example 2
  2. customto obtain 960 mg of a crude product
  3. customThe refined product was recrystallized from a mixed solvent of chloroform/ethanol (20/80)

Sources & evidence

ORD record
ord-fc89fe288a7546b1a90e04fb45cce457
Source dataset
uspto-grants-1991_10
Patent number
US05059345

Reaction notes

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