Hydrochloric Acid → 3-acetyl-5-propyldihydrofuran-2(3h)-one

HRID 2081281Notes

Reaction equation

HRID 2081281 reaction equation
[C:1]([O:7][CH2:8][CH2:9][CH2:10][CH2:11]CCCC)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[CH2:16]1OC1CCC.[OH-].[Na+].Cl>O>[C:3]([CH:2]1[CH2:16][CH:8]([CH2:9][CH2:10][CH3:11])[O:7][C:1]1=[O:6])(=[O:4])[CH3:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 13853Oxirane, 2-propyl-HCID 14798Sodium HydroxideHCID 85418Octyl acetoacetate

Product 1

HCID 2402563-acetyl-5-propyldihydrofuran-2(3h)-oneYield 62.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
24 °C

Procedure

n-Octyl acetoacetate (313.3 g, 1.42 moles), 1,2-pentylene oxide 101.8 g, 1.18 moles) and 157.5 g distilled water were combined in a reactor. A solution of 59.6 g sodium hydroxide (1.49 moles) in 59.6 g distilled water was added over a one-hour period while maintaining the temperature in the range of 22 to 26° C. The reaction mixture was then allowed to stir for an additional 111/2 hours while maintaining the temperature between 28° C. and 36° C. The reaction mixture was then acidified to pH 5.8 by the addition of concentrated hydrochloric acid. After separation of the organic and aqueous phases, the organic layer was stripped under reduced pressure to remove the n-octanol and any unreacted n-octyl acetoactetate. 3-Acetyl-5-propyldihydro-2(3H)-furanone ##STR12## was recovered upon distillation in 62.4% yield.

Workup

  1. customwere combined in a reactor
  2. additionwas added over a one-hour period
  3. temperaturewhile maintaining the temperature between 28° C. and 36° C
  4. customAfter separation of the organic and aqueous phases
  5. customto remove the n-octanol
  6. distillation3-Acetyl-5-propyldihydro-2(3H)-furanone ##STR12## was recovered upon distillation in 62.4% yield

Sources & evidence

ORD record
ord-d990d608f0fd43f49ce4bceaeb1e6d02
Source dataset
uspto-grants-1993_02
Patent number
US05183908

Reaction notes

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