Sulfuric Acid → HCID 58566715, compound

HRID 445865Notes

Reaction equation

HRID 445865 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[Cl:9][CH2:10][C:11]([CH3:13])=[CH2:12].S(=O)(=O)(O)O>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:11]([CH3:13])([CH3:12])[CH2:10][Cl:9])[CH:3]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 46844-ChlorophenolHCID 112413-Chloro-2-methyl-1-propene

Product 1

HCID 58566715HCID 58566715, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-chlorophenol (12.6 g, 0.1 mol) and 3-chloro-2-methyl-propene (10.8 g, 0.12 mol) was added concentrated sulfuric acid (5 g, 0.05 mol) and stirred at 0° C. for 1 hour. The mixture was diluted with cold water and extracted with ether. The ethereal extract was washed with brine, dried over anhydrous sodium sulfate, filtered, and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel to afford 4-chloro-2-(1-chloro-2-methylpropan-2-yl)phenol (721).

Workup

  1. extractionextracted with ether
  2. extractionThe ethereal extract
  3. washwas washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-c4be6813357c4f7399b981240357b075
Source dataset
uspto-grants-2013_07
Patent number
US08476308B2

Reaction notes

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