Hydrochloric Acid → 1,3-Diisobutyryloxy-2-phenyl-2-propanol

HRID 1003771Notes

Reaction equation

HRID 1003771 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:9]([O:14][CH2:15][C:16]([CH2:18][O:19][C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])=[O:17])(=[O:13])[CH:10]([CH3:12])[CH3:11].Cl>C(OCC)C>[C:9]([O:14][CH2:15][C:16]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)([OH:17])[CH2:18][O:19][C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])(=[O:13])[CH:10]([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7961BromobenzeneHCID 5462224MagnesiumHCID 155218061,3-Diisobutyryloxyacetone

Product 1

HCID 187986191,3-Diisobutyryloxy-2-phenyl-2-propanolYield 108.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
-50 °C

Procedure

Under an atmosphere of argon, 2 ml of diethyl ether was slowly added to 695 mg of magnesium turnings, and then thereto was added dropwise 4 g of bromobenzene dissolved in 10 ml of diethyl ether. The resulting liquid was stirred for 1 hour under refluxing and allowed to cool. That liquid was added dropwise to 50 ml of diethyl ether solution of 3.78 g of 1,3-diisobutyryloxyacetone which was previously cooled to -50° C. After the resulting liquid was stirred at -50° C. for 1 hour, a temperature thereof was gradually raised to room temperature. Then, the reaction mixture was added to 50 ml of 2 N aqueous solution of hydrochloric acid at 5° C. or below, and an organic layer was separated and the aqueous layer was extracted twice with 50 ml of ethyl acetate. The organic layers were combined and washed three times with 1N aqueous solution of sodium hydroxide, washed twice with saturated aqueous solution with sodium chloride, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1) to give 5.5 g of the desired compound.

Workup

  1. temperatureunder refluxing
  2. temperatureto cool
  3. stirringAfter the resulting liquid was stirred at -50° C. for 1 hour
  4. temperaturea temperature thereof was gradually raised to room temperature
  5. customan organic layer was separated
  6. extractionthe aqueous layer was extracted twice with 50 ml of ethyl acetate
  7. washwashed three times with 1N aqueous solution of sodium hydroxide
  8. washwashed twice with saturated aqueous solution with sodium chloride
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was removed under reduced pressure
  11. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-bea7219be1a64b41b972ed4c93bf79b3
Source dataset
uspto-grants-2000_04
Patent number
US06046354

Reaction notes

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