4,4'-Dihydroxybiphenyl → HCID 19887240, compound

HRID 654417Notes

Reaction equation

HRID 654417 reaction equation
Br[CH2:2][CH2:3][O:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:5]([O:4][CH2:3][CH2:2][O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[CH:14][CH:15]=1)[CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 71124,4'-DihydroxybiphenylHCID 11430Potassium CarbonateHCID 1387612-Butoxyethyl bromide

Product 1

HCID 19887240HCID 19887240, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

One gram (5.5 millimoles) of 1-bromo-2-butoxyethane was combined with 5.5 grams (30 millimoles) of 4,4'-dihydroxybiphenyl in 75 mls. of acetonitrile. To the reaction mixture were added 8.3 grams (60 millimoles) of finely ground potassium carbonate. Stirring was begun and the reaction mixture was brought to reflux and maintained for 48 hours. The reaction product was filtered, washed with acetonitrile and evaporated for removal of solvent. The product was passed through a silica gel chromatographic column using dichloromethane eluent, for recovery of 0.25 gram (20% yield) of a biphenol ether compound having the following formula confirmed by TLC, IR and mass spectral analyses: ##STR26##

Workup

  1. temperatureto reflux
  2. temperaturemaintained for 48 hours
  3. filtrationThe reaction product was filtered
  4. washwashed with acetonitrile
  5. customevaporated for removal of solvent

Sources & evidence

ORD record
ord-cc03d9841e7b41ffb2eb7a7d00bd189c
Source dataset
uspto-grants-1992_07
Patent number
US05132041

Reaction notes

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