Methanol → 4-tert-Butyl-2-chlorophenol

HRID 1915315Notes

Reaction equation

HRID 1915315 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CO.O.C(Cl)[Cl:16]>>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([OH:11])=[C:9]([Cl:16])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 6344DichloromethaneHCID 73934-tert-Butylphenol

Product 1

HCID 73804-tert-Butyl-2-chlorophenolYield 95%

Procedure

To a solution of 4-tert-butyl-phenol (40.0 g, 0.27 mol) and SO2Cl2 (37.5 g, 0.28 mol) in CH2Cl2 was added MeOH (9.0 g, 0.28 mol) at 0° C. After addition was complete, the mixture was stirred overnight at room temperature and then water (200 mL) was added. The resulting solution was extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under vacuum. The residue was purified by column chromatography (Pet. Ether/EtOAc, 50:1) to give 4-tert-butyl-2-chloro-phenol (47.0 g, 95%).

Workup

  1. additionAfter addition
  2. extractionThe resulting solution was extracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by column chromatography (Pet. Ether/EtOAc, 50:1)

Sources & evidence

ORD record
ord-82f1356262924245aae81f63d7be5782
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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