Phenol → 2,2'-Bis(phenoxymethyl)biphenyl

HRID 363824Notes

Reaction equation

HRID 363824 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15]Br.[C:17]1([OH:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH-:24].[K+]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.ClCCl>[O:23]([CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][O:24][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 14797Potassium HydroxideHCID 2519622,2'-Bis(bromomethyl)-1,1'-biphenyl

Product 1

HCID 537376072,2'-Bis(phenoxymethyl)biphenyl

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 25.0 g (73.5 mmol) of 2,2'-bis(bromomethyl)biphenyl, 14.2 g (151 mmol) of phenol, 14.7 g (261 mmol) of pulverized potassium hydroxide and 3.41 g (15 mmol) of triethylbenzylammonium chloride is admixed with 120 ml of dichloromethane and stirred for 5 hours at 40° C.

Sources & evidence

ORD record
ord-9668b42c33fa4570bcfe893d5ace0f55
Source dataset
uspto-grants-1999_02
Patent number
US05874642

Reaction notes

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