Sulfuric Acid → HCID 21314004, compound

HRID 971443Notes

Reaction equation

HRID 971443 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](=[O:12])[CH3:11])=[CH:4][CH:3]=1.[CH3:13][Mg]I.S(=O)(=O)(O)O>CCOCC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([CH3:13])([OH:12])[CH3:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 12814692HCID 12814692, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 21314004HCID 21314004, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

4-(4-Fluorophenyl)-2-butanone (10.0 g) in ether (30 ml) was added over 20 min. to a stirred solution of methyl magnesium iodide (0.086 mole) in ether (80 ml). The mixture was stirred at room temperature over 5 hr, then cooled and 2 M sulphuric acid (30 ml) added. The mixture was extracted with ether (5×50 ml), washed with saturated sodium bicarbonate solution, saturated brine and dried (MgSO4). The solvent was removed and the residue was distilled. The alcohol (9.4 g) b.p. 83°-85°/0.1 mm was obtained as a colourless liquid.

Workup

  1. temperaturecooled
  2. extractionThe mixture was extracted with ether (5×50 ml)
  3. washwashed with saturated sodium bicarbonate solution, saturated brine
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed
  6. distillationthe residue was distilled

Sources & evidence

ORD record
ord-5fe0bcc3ac48498a9becedf6258d3d34
Source dataset
uspto-grants-1979_07
Patent number
US04160036

Reaction notes

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