Catechol → o-[p-(4-Phenylbutoxy)benzyloxy]phenol

HRID 982221Notes

Reaction equation

HRID 982221 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.[C:20]1([C:22](=[CH:24][CH:25]=[CH:26][CH:27]=1)[OH:23])[OH:21].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[C:14]1([CH2:13][CH2:12][CH2:11][CH2:10][O:9][C:6]2[CH:7]=[CH:8][C:3]([CH2:2][O:21][C:20]3[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=3[OH:23])=[CH:4][CH:5]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 289CatecholHCID 11430Potassium CarbonateHCID 151155321-(Chloromethyl)-4-(4-phenylbutoxy)benzene

Product 1

HCID 19882704o-[p-(4-Phenylbutoxy)benzyloxy]phenolYield 48.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In 1.5 ml of N,N-dimethylformamide were stirred 390 mg of 4-chloromethyl-1-(4-phenylbutoxy)benzene, 180 mg of catechol and 270 mg of potassium carbonate at room temperature overnight. The reaction mixture was dispersed in water and ethyl acetate and the dispersion was separated. The ethyl acetate layer washed subsequently with water and an aqueous saline solution, dried and concentrated. The obtained residue was applied to silica gel column chromatography and eluted with toluene to obtain 240 mg of o-[p-(4-phenylbutoxy)benzyloxy]phenol.

Workup

  1. customethyl acetate and the dispersion was separated
  2. washThe ethyl acetate layer washed subsequently with water
  3. customan aqueous saline solution, dried
  4. concentrationconcentrated
  5. washeluted with toluene

Sources & evidence

ORD record
ord-09361c771f814a5ab984e5fe67d8a740
Source dataset
uspto-grants-1991_02
Patent number
US04994479

Reaction notes

Loading…