4,4'-Dihydroxybiphenyl → 4'-(3-Hydroxypropoxy)biphenyl-4-ol

HRID 1873382Notes

Reaction equation

HRID 1873382 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=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:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 71124,4'-DihydroxybiphenylHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanol

Product 1

HCID 160378654'-(3-Hydroxypropoxy)biphenyl-4-ol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

20.0 g (0.107 mol) of 4,4′-dihydroxybiphenyl, 10.0 g (0.070 mol) of 3-bromo-1-propanol and 15.0 g (0.109 mol) of potassium carbonate are heated under reflux in 300 ml of acetone for 16 h. The batch is subsequently filtered, and the filtrate is evaporated. The residue is taken up in MTB ether, washed with water and dried over sodium sulfate. The solvent is removed in vacuo, and the crude product is chromatographed on silica gel with toluene/ethyl acetate (1:1). Crystallisation from toluene/ethyl acetate gives 4′-(3-hydroxypropoxy)biphenyl-4-ol as a colourless solid.

Workup

  1. filtrationThe batch is subsequently filtered
  2. customthe filtrate is evaporated
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is removed in vacuo
  6. customthe crude product is chromatographed on silica gel with toluene/ethyl acetate (1:1)
  7. customCrystallisation from toluene/ethyl acetate

Sources & evidence

ORD record
ord-22498c1307ab42acab4957d82ffb07a5
Source dataset
uspto-grants-2012_11
Patent number
US08304035B2

Reaction notes

Loading…