Sulfuric Acid → HCID 22731307, compound

HRID 2085567Notes

Reaction equation

HRID 2085567 reaction equation
[Br: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>[Br: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 78084-BromophenolHCID 112413-Chloro-2-methyl-1-propene

Product 1

HCID 22731307HCID 22731307, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred, cooled (ice bath) mixture of 4-bromophenol (0.512 g, 3 mmol) and 3-chloro-2-methylpropene (0.32 mL, 3.3 mmol), concentrated sulfuric acid (0.1 mL, 1.5 mmol) was added and the dark reaction mixture was stirred for 1 h. The reaction 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 to an oil. Flash column chromatography of the oil over silica gel (230-400 mesh) using 5% ethyl acetate in hexane as the eluent afforded the title compound as an oil (0.33 g, 42.6%). Some dialkylated product was also formed and some starting material was recovered.

Workup

  1. temperatureTo a stirred, cooled
  2. additionwas added
  3. customthe dark reaction mixture
  4. extractionextracted with ether
  5. extractionThe ethereal extract
  6. washwas washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated to an oil

Sources & evidence

ORD record
ord-6987e481ccfc464a9d14f37eb7f9d5fc
Source dataset
uspto-grants-2004_04
Patent number
US06720423B2

Reaction notes

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