Phenol → Dibenzyl ether

HRID 841044Notes

Reaction equation

HRID 841044 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]1(O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:16](=O)([O-])[O-:17].[K+].[K+]>CN(C=O)C>[CH2:1]([O:17][CH2:16][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 7657Dibenzyl ether

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

A solution of benzyl bromide (128 mg, 0.75 mmol), phenol compound 40 (131.5 mg, 0.50 mmol), and potassium carbonate (138 mg, 1.00 mmol) in DMF (3.0 mL) was heated to 60° C. for 1.5 h. After cooling to 23° C., the solution was filtered, concentrated in vacuo, and purified by silica gel chromatography (1:1 EtOAc/hexanes) to give benzyl ether compound 49 (132.5 mg, 75%) as a white solid. mp=124-125° C.; 1H NMR (CDCl3) δ 7.67 (s, 1H), 7.49 (s, 1H), 7.40 (m, 6H), 6.0-5.8 (2 br s, 2H), 5.08 (s, 2H); IR (KBr pellet) 3369, 3192, 1660, 1564 cm−1; Anal. (C14H12INO2) C, H, N.

Workup

  1. filtrationthe solution was filtered
  2. concentrationconcentrated in vacuo
  3. custompurified by silica gel chromatography (1:1 EtOAc/hexanes)

Sources & evidence

ORD record
ord-21b0dbea9e624a5eab04114e148b1e26
Source dataset
uspto-grants-2002_04
Patent number
US06369226B1

Reaction notes

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