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

HRID 385709Notes

Reaction equation

HRID 385709 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-61d0ccc73edd4c0d8a1fa039bb5e8d42
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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