Sulfuric Acid → 2-(2-Chloro-6-fluorophenyl)propan-2-ol

HRID 2256967Notes

Reaction equation

HRID 2256967 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:3]=1C(OC)=O.[CH3:13][Mg]I.S(=O)(=O)(O)O.CC[O:23][CH2:24][CH3:25]>>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:3]=1[C:24]([OH:23])([CH3:25])[CH3:13]

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 3283Diethyl Ether2×HCID 593924Methyl 2-chloro-6-fluorobenzoateHCID 178418373HCID 178418373, compound

Product 1

HCID 540290942-(2-Chloro-6-fluorophenyl)propan-2-ol

Procedure

A solution of methyl 2-chloro-6-fluorobenzoate (40.0 g) in ether was added to a solution of methyl magnesium iodide in ether (prepared from methyl iodide (120.0 g) and magnesium turnings (20.6 g) in ether). The resulting solution was stirred and heated at reflux for 5 hours, poured onto a mixture of ice and concentrated sulphuric acid and the layers separated. The organic layer was washed with water, saturated aqueous sodium bisulphite, water, dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness to give 2-(2-chloro-6-fluorophenyl)-propan-2-ol (36.8 g) as an orange oil, NMR (CDCl3) 1.8(d, 6H), 3.5-3.7(bs,1H), 6.9-7.05(m,1H), 7.1-7.25(m,2H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 hours
  3. customthe layers separated
  4. washThe organic layer was washed with water, saturated aqueous sodium bisulphite, water
  5. dry with materialdried (anhydrous magnesium sulphate)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-18ad16bf03c8413bbc2834b88979306e
Source dataset
uspto-grants-1997_08
Patent number
US05656573

Reaction notes

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