4,4'-Dihydroxybiphenyl → HCID 14365850, compound

HRID 442596Notes

Reaction equation

HRID 442596 reaction equation
[CH:1]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)=[CH:5][CH:4]=[C:3]([OH:14])[CH:2]=1.C(N(CC)CC)C.[C:22](Cl)(=[O:31])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].CC1C(C)=NC=CC=1>ClCCl>[C:22]([O:14][C:3]1[CH:2]=[CH:1][C:6]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)=[CH:5][CH:4]=1)(=[O:31])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

6

Reactant 4

HCID 71124,4'-DihydroxybiphenylHCID 8471TriethylamineHCID 114202,3-LutidineHCID 69819Nonanoyl chloride

Product 1

HCID 14365850HCID 14365850, compoundYield 159.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4,4'-Diphenol (0.1 g) and triethylamine (0.57 g) were dissolved in dichloromethane (20 ml). Nonanoyl chloride (1.0 g) and dimethylpyridine (0.2 g) were added thereto, and the mixture was stirred at room temperature for about 20 hours. The reaction mixture was poured into ice-water and subjected to extraction with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and removed by evaporation to give a crude product. It was purified by silica gel column chromatography (developer: hexane/ethyl acetate=3/2) to give the titled compound (0.28 g).

Workup

  1. extractionsubjected to extraction with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customremoved by evaporation
  4. customto give a crude product
  5. customIt was purified by silica gel column chromatography (developer: hexane/ethyl acetate=3/2)

Sources & evidence

ORD record
ord-a1118b6b8f38457e82f9ca91f9a3e00a
Source dataset
uspto-grants-1999_04
Patent number
US05891359

Reaction notes

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