4,4'-Dihydroxybiphenyl → 4-(2-Methyloctanoyl) benzoic acid 4-hydroxy biphenyl

HRID 846568Notes

Reaction equation

HRID 846568 reaction equation
[CH3:1][CH:2]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)=[O:4].[CH:20]1[C:25]([C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)=[CH:24][CH:23]=[C:22](O)[CH:21]=1.C1(N=C=NC2CCCCC2)CCCCC1>N1C=CC=CC=1>[CH3:1][CH:2]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)=[O:4].[OH:32][C:29]1[CH:28]=[CH:27][C:26]([C:25]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 71124,4'-DihydroxybiphenylHCID 10868DicyclohexylcarbodiimideHCID 198829064-(2-Methyloctanoyl) benzoic acid

Product 1

HCID 679137834-(2-Methyloctanoyl) benzoic acid 4-hydroxy biphenylYield 49%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Into a flask were charged 151.0 mg (0.58 mmol) of 4-(2-methyloctanoyl) benzoic acid, 321.3 mg (1.74 mmol) of p,p'-biphenol, N,N'-dicyclohexyl-carbodiimide (0.66 mmol) and 6 ml of dried pyridine, which was stirred at room temperature for 6 hours. The resulting solid was filtered off and the solvent was distilled off, and the resulting oily matter was purified by a column chromatography of silica gel to obtain 122.3 mg (yield 49%) of 4-(2-methyloctanoyl) benzoic acid-4-hydroxy biphenyl.

Workup

  1. filtrationThe resulting solid was filtered off
  2. distillationthe solvent was distilled off
  3. customthe resulting oily matter was purified by a column chromatography of silica gel

Sources & evidence

ORD record
ord-19a5ccdc680d45a8a1ae1eab7e6bd19f
Source dataset
uspto-grants-1992_08
Patent number
US05137653

Reaction notes

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