Hydrochloric Acid → HCID 58335273, compound

HRID 2060643Notes

Reaction equation

HRID 2060643 reaction equation
C([O:3][CH:4](OCC)[C:5]1[CH:10]=[CH:9][C:8]([C:11]([OH:14])([CH3:13])[CH3:12])=[CH:7][C:6]=1[F:15])C.Cl>CC(C)=O>[F:15][C:6]1[CH:7]=[C:8]([C:11]([OH:14])([CH3:12])[CH3:13])[CH:9]=[CH:10][C:5]=1[CH:4]=[O:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58335259HCID 58335259, compound

Product 1

HCID 58335273HCID 58335273, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2-[4-(diethoxymethyl)-3-fluorophenyl]propan-2-ol (25.6 g, 100 mmol) in acetone (50 mL) was added dropwise to aqueous HCl (6M, 50 mL) cooled with ice-water to keep the internal temperature less than 10° C. After addition, the mixture was stirred at room temperature for 6 hrs. The mixture was extracted twice with ethyl acetate. The combined organics were washed with saturated aqueous sodium bicarbonate and brine, dried over sodium sulfate and concentrated to afford the title compound. 1H NMR (300 MHz, CDCl3): δ 10.23 (s, 1H), 7.81 (d, 1H), 7.34 (d, 1H), 7.30 (d, 1H), 2.01 (s, 1H), 1.49 (s, 61-1).

Workup

  1. customthe internal temperature less than 10° C
  2. additionAfter addition
  3. extractionThe mixture was extracted twice with ethyl acetate
  4. washThe combined organics were washed with saturated aqueous sodium bicarbonate and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b333625433eb43ddbb75f1cc72048106
Source dataset
uspto-grants-2012_10
Patent number
US08278335B2

Reaction notes

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