Hydrochloric Acid → [2,6-Difluoro-4-(1-hydroxy-1-methyl-ethyl)-phenyl]-acetaldehyde

HRID 1799535Notes

Reaction equation

HRID 1799535 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:13]([OH:16])([CH3:15])[CH3:14])[CH:5]=[C:6]([F:12])[C:7]=1[CH:8]=[CH:9][O:10]C.Cl>CC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([C:13]([OH:16])([CH3:14])[CH3:15])[CH:5]=[C:6]([F:12])[C:7]=1[CH2:8][CH:9]=[O:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 670288782-{3,5-Difluoro-4-[2-methoxyvinyl]phenyl}propan-2-ol

Product 1

HCID 59525773[2,6-Difluoro-4-(1-hydroxy-1-methyl-ethyl)-phenyl]-acetaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2-{3,5-difluoro-4-[2-methoxyvinyl]phenyl}propan-2-ol (5.0 g, 22 mmol) in acetone (25 mL) was added dropwise to 4 M aqueous hydrochloric acid (25 mL, 100 mmol) with ice-water cooling, keeping the temperature below 10° C. Then the mixture was stirred at room temperature for six hours. The resulting mixture was extracted with ethyl acetate (2×) and the combined organic phases were washed with saturated aqueous sodium bicarbonate and brine. The organic layer was then dried and concentrated in vacuo to afford the title compound.

Workup

  1. customthe temperature below 10° C
  2. extractionThe resulting mixture was extracted with ethyl acetate (2×)
  3. washthe combined organic phases were washed with saturated aqueous sodium bicarbonate and brine
  4. customThe organic layer was then dried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2bb9eb1ddd804cc798f7e3655950dcd1
Source dataset
uspto-grants-2013_01
Patent number
US08344144B2

Reaction notes

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