Allyl Alcohol → HCID 13005704, compound

HRID 2060746Notes

Reaction equation

HRID 2060746 reaction equation
C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+].[CH2:20]([OH:23])[CH:21]=[CH2:22].Br[CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27]>O.C1(C)C=CC=CC=1>[CH2:20]([O:23][CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:21]=[CH2:22]

Participants

7

Reactant 4

HCID 7858Allyl AlcoholHCID 14798Sodium HydroxideHCID 16028TetrabutylammoniumHCID 79177tert-Butyl bromoacetate

Product 1

HCID 13005704HCID 13005704, compoundYield 109.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

Tetrabutylammonium hydrogenosulfate (470 g, 1.40 mol) is added to a solution of sodium hydroxide (6.6 Kg, 165 mol) in water (14 L) and toluene (14 L) at 20° C. Allyl alcohol (801.5 g, 13.8 mol) is added and the mixture is stirred at 20° C. for 1 h. The mixture is cooled to 5° C., and tert-butyl 2-bromoacetate (4 Kg, 20.5 mol) is added slowly maintaining the internal temperature below 15° C. The reaction mixture is stirred at room temperature for 16 h. The mixture is diluted with water (12 L) and hexanes (12 L) and the organic phase is separated. The aqueous phase is extracted with MTBE (5 L). The combined organic phase is dried over magnesium sulfate, filtered, and concentrated to afford the title compound as colorless oil (2.6 Kg, 100%). ES/MS m/e: 173 (M+1).

Workup

  1. temperatureThe mixture is cooled to 5° C.
  2. temperaturemaintaining the internal temperature below 15° C
  3. stirringThe reaction mixture is stirred at room temperature for 16 h
  4. customthe organic phase is separated
  5. extractionThe aqueous phase is extracted with MTBE (5 L)
  6. dry with materialThe combined organic phase is dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3cc4a2cda5ea41469ea6788e45be7925
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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