Water → 2-(2-(Biphenyl-2-yl)ethoxy)ethanol

HRID 1451514Notes

Reaction equation

HRID 1451514 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][OH:9].Br[CH2:17][CH2:18][O:19]C1CCCCO1.[OH-].[K+].O>CS(C)=O>[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][O:9][CH2:17][CH2:18][OH:19]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyran2×HCID 22052021[1,1'-Biphenyl]-2-ethanol

Product 1

HCID 199747032-(2-(Biphenyl-2-yl)ethoxy)ethanol

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of the alcohol prepared above (8.5 g, 43 mmol), 2-bromoethyltetrahydro-2-pyranylether (17.9 g, 86 mmol) and potassium hydroxide (9.6 g, 171 mmol) in dimethylsulfoxide (100 ml) was stirred at ambient temperature for 72 h. An extra batch of 2-bromoethyltetrahydro-2-pyranylether (3.6 g, 17 mmol) was added and the mixture stirred for 48 h at ambient temperature. Water (350 ml) was added and the mixture was extracted with diethylether (2×250 ml). The organic phases were combined, washed with water (100 ml), dried (MgSO4) and concentrated in vacuo. The residue was submitted to column chromatography on silica gel (400 ml) using heptane and ethyl acetate (3:2) as eluent to give 6.6 g of 2-(2-(biphenyl-2-yl)ethoxy)ethanol as an oil.

Workup

  1. stirringthe mixture stirred for 48 h at ambient temperature
  2. extractionthe mixture was extracted with diethylether (2×250 ml)
  3. washwashed with water (100 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1f3491e4772f4597b8a1e5972a4e83af
Source dataset
uspto-grants-1997_02
Patent number
US05604242

Reaction notes

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