Catechol → o-(p-Nitrophenoxy)phenol

HRID 1796614Notes

Reaction equation

HRID 1796614 reaction equation
CC([O-])(C)C.[K+].[C:7]1([C:9](=[CH:11][CH:12]=[CH:13][CH:14]=1)[OH:10])[OH:8].F[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1.Cl>CC(N(C)C)=O>[N+:22]([C:19]1[CH:20]=[CH:21][C:16]([O:8][C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[OH:10])=[CH:17][CH:18]=1)([O-:24])=[O:23]

Participants

6

Reactant 4

HCID 289CatecholHCID 313Hydrochloric AcidHCID 9590p-FluoronitrobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 3016048o-(p-Nitrophenoxy)phenolYield 53%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Conditions

Temperature
120 °C

Procedure

Anhydrous DMA (50 ml) was added to t-BuOK (5.46 g, 48.7 mmol) and catechol (5.00 g, 45.4 mmol) at 0° C. under argon, the mixture was heated to 120° C. over 10 min. A solution of 1-fluoro-4-nitro-benzene (6.40 g, 45.4 mmol) in anhydrous DMA (10 ml) was added dropwise over 20 min. The reaction mixture was then stirred at 130° C. for 1.5 h, cooled, and poured into 1N HCl (200 ml), extracted with EtOAc (2×50 ml). The combined extract was washed H2O (3×150 ml), brine (150 ml), dried with Na2SO4, concentrated and purified by silica gel flash column chromatography to give desired product 388A (5.56 g, 53%) as a faintly yellow solid (0%-1% ethyl acetate-CH2Cl2).

Workup

  1. temperaturecooled
  2. extractionextracted with EtOAc (2×50 ml)
  3. extractionThe combined extract
  4. washwas washed H2O (3×150 ml), brine (150 ml)
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated
  7. custompurified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-6a459796b4ce40929ada5e2055e53b08
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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