Potassium Carbonate → 3'-(3-Hydroxypropoxy)biphenyl-3-ol

HRID 1877707Notes

Reaction equation

HRID 1877707 reaction equation
[C:1]1([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[CH:9]=2)[CH:6]=[CH:5][CH:4]=[C:3]([OH:7])[CH:2]=1.Br[CH2:16][CH2:17][CH2:18][OH:19].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[OH:19][CH2:18][CH2:17][CH2:16][O:14][C:10]1[CH:9]=[C:8]([C:1]2[CH:6]=[CH:5][CH:4]=[C:3]([OH:7])[CH:2]=2)[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 691653,3'-Biphenyldiol

Product 1

HCID 582395993'-(3-Hydroxypropoxy)biphenyl-3-ol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

26.0 g (0.140 mol) of biphenyl-3,3′-diol and 10.0 g of 3-bromo-1-propanol are dissolved in 300 ml of acetone, and, after addition of 19.3 g (0.140 mol) of potassium carbonate, the mixture is heated under reflux overnight. The batch is subsequently filtered and evaporated, and the residue is chromatographed on silica gel with toluene/ethyl acetate (1:1), giving 3′-(3-hydroxypropoxy)biphenyl-3-ol as colourless crystals.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux overnight
  3. filtrationThe batch is subsequently filtered
  4. customevaporated
  5. customthe residue is chromatographed on silica gel with toluene/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-03f122dcbd154e85b85f04a9e58d140a
Source dataset
uspto-grants-2012_11
Patent number
US08313669B2

Reaction notes

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