Sodium Hydroxide → 2,6-Dichloro-m-cresol

HRID 1875131Notes

Reaction equation

HRID 1875131 reaction equation
Br[C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[C:4]([Cl:10])[C:3]=1[CH3:11].[OH-].[Na+]>[Zn]>[Cl:10][C:4]1[C:3]([CH3:11])=[CH:2][CH:7]=[C:6]([Cl:8])[C:5]=1[OH:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 156210804-Bromo-2,6-dichloro-3-methylphenol

Product 1

HCID 835212,6-Dichloro-m-cresolYield 88%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Conditions

Temperature
100 °C

Procedure

Zn powder (9.84 g, 150 mmol) was added to a solution of 4-bromo-2,6-dichloro-3-methylphenol (4.92 g, 19.22 mmol) in 10% NaOH (50 ml, 125 mmol). The reaction mixture was stirred for 1 h at 100° C. and then cooled down to RT. The Zn powder was filtered off and the filtrate was acidified with 10% HCl and extracted with CH2Cl2. The combined organic extracts were dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel eluted with 0-5% EtOAc in hexane to give the title compound as a colorless oil (2.98 g, 88%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.14 (1H, d) 6.76 (1H, d) 5.83 (1H, s) 2.34 (3H, s). LCMS: m/z 175 (M−1).

Workup

  1. temperaturecooled down to RT
  2. filtrationThe Zn powder was filtered off
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel
  8. washeluted with 0-5% EtOAc in hexane

Sources & evidence

ORD record
ord-e4668ad99e074991832bfbb4ec7712c8
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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