Hydrochloric Acid → 2-Chloro-3,6-difluoro-α-methylbenzenemethanol

HRID 1766733Notes

Reaction equation

HRID 1766733 reaction equation
[Cl:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([F:11])[C:3]=1[CH:4]=[O:5].[CH3:12][Mg]Cl.CO.Cl>C1COCC1.C(OCC)(=O)C>[Cl:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([F:11])[C:3]=1[CH:4]([OH:5])[CH3:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 27735092-Chloro-3,6-difluorobenzaldehydeHCID 178418332HCID 178418332, compound

Product 1

HCID 211113742-Chloro-3,6-difluoro-α-methylbenzenemethanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

2-Chloro-3,6-difluorobenzaldehyde (1.0 molar equivalent) was dissolved in THF (0.2 M) and stirred at 0° C. for 5 min. The corresponding methylmagnesium chloride solution (1.1 molar equivalent) was added. The reaction was warmed up gradually to ambient temperature and stirred for 2 hr. Methanol, and 1 N HCl was added to the mixture and diluted with ethyl acetate. The mixture was washed with water, brine, dried over MgSO4, filtered, and concentrated to give 1-(2-chloro-3,6-difluoro-phenyl)-ethanol as oil. 1H NMR (400 MHz, DMSO-d6) δ 1.42 (d, 3H), 5.21 (m, 1H), 5.42 (m, 1H), 7.09 (m, 1H), 7.18 (m, 1H).

Workup

  1. temperatureThe reaction was warmed up gradually to ambient temperature
  2. stirringstirred for 2 hr
  3. washThe mixture was washed with water, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e8374f343be64c1d9befdcc40dcbea0c
Source dataset
uspto-grants-2007_06
Patent number
US07230098B2

Reaction notes

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