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

HRID 1799531Notes

Reaction equation

HRID 1799531 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:12]([OH:15])([CH3:14])[CH3:13])[CH:5]=[CH:6][C:7]=1[CH:8]=[CH:9][O:10]C.Cl>CC(C)=O.O.C(OCC)C>[F:1][C:2]1[CH:3]=[C:4]([C:12]([OH:15])([CH3:14])[CH3:13])[CH:5]=[CH:6][C:7]=1[CH2:8][CH:9]=[O:10]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 671174472-{3-Fluoro-4-[2-methoxyvinyl]phenyl}propan-2-ol

Product 1

HCID 58216657[2-Fluoro-4-(1-hydroxy-1-methyl-ethyl)-phenyl]-acetaldehyde

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a room temperature solution of 2-{3-fluoro-4-[2-methoxyvinyl]phenyl}propan-2-ol (100 mg, 0.48 mmol) in acetone (5 mL) was added dropwise 4 M aqueous hydrochloric acid (5 mL, 20 mmol). The reaction was stirred at room temperature for two hours. The mixture was then diluted with 25 mL of water and 50 mL of diethyl ether. The water phase was extracted with diethyl ether (2×) and the combined organic layers were washed with saturated aqueous sodium bicarbonate and brine, dried and concentrated in vacuo to afford the title compound.

Workup

  1. extractionThe water phase was extracted with diethyl ether (2×)
  2. washthe combined organic layers were washed with saturated aqueous sodium bicarbonate and brine
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a0826d516cef47e899659406f0933840
Source dataset
uspto-grants-2013_01
Patent number
US08344144B2

Reaction notes

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