Phenol → Diphenyl Ether

HRID 1169634Notes

Reaction equation

HRID 1169634 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8]1(CCCCO)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(P(CCCC)CCCC)CCC.N(C(N(C)C)=O)=NC(N(C)C)=O>ClCCl.O1CCCC1>[C:1]1([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 76889Benzenebutanol

Product 1

HCID 7583Diphenyl EtherYield 139.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the phenol resin (100 mg), 4-phenylbutan-1-ol (0.42 mmol) was added at room temperature, followed by the addition of dry tetrahydrofuran (0.4 mL) and dichloromethane (0.4 mL). At room temperature, tri-n-butylphosphine (0.42 mmol) was added dropwise thereto and further 1,1′-azobis(N,N-dimethylformamide) (0.42 mmol) was added. The mixture was shaken at room temperature for 5 hours. The resin was taken up by filtration, washed with a mixed solvent (dichloromethane:tetrahydrofuran=1:1) 4 times and dichloromethane 2 times and then dried to give a phenyl ether resin (about 100 mg).

Workup

  1. filtrationThe resin was taken up by filtration
  2. washwashed with a mixed solvent (dichloromethane:tetrahydrofuran=1:1) 4 times and dichloromethane 2 times
  3. customdried

Sources & evidence

ORD record
ord-fc501fe4267e432a9bda0f1e571bca42
Source dataset
uspto-grants-2010_11
Patent number
US07825109B2

Reaction notes

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