Hydrochloric Acid → 4-Acetoxy-2-methyl-2-buten-1-ol

HRID 260567

Reaction equation

HRID 260567 reaction equation
C(=O)(O)[O-].[Na+].C([O:8][CH2:9][C:10]([CH3:17])=[CH:11][CH2:12][O:13][C:14](=[O:16])[CH3:15])=O.O.Cl>CO.C(OCC)(=O)C>[C:14]([O:13][CH2:12][CH:11]=[C:10]([CH3:17])[CH2:9][OH:8])(=[O:16])[CH3:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 543352444-Acetoxy-2-methyl-2-buten-1-ol formate

Product 1

HCID 5382224-Acetoxy-2-methyl-2-buten-1-olYield 97.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium bicarbonate (0.40 g, 4.75 mmol, 10 mol %) was added to a solution of 4-acetoxy-2-methyl-2-buten-1-ol formate (8.18 g, 47.5 mmol) in methanol (40 ml). The mixture was stirred at room temperature for 2 hours. After completion of the reaction, most of the methanol was evaporated under reduced pressure. The resulting reaction mixture was poured into a mixture of ice-cooled water (20 ml) and ethyl acetate (100 ml). The pH of the aqueous layer was adjusted to 5 to 6 with 1N hydrochloric acid, and the ethyl acetate layer was separated. The aqueous layer was extracted with ethyl acetate (50 ml) twice. The ethyl acetate layers were combined and dried over anhydrous sodium sulfate. Evaporation of the ethyl acetate gave 4-acetoxy-2-methyl-2-buten-1-ol (6.69 g, 46.4 mmol; Yield: 97.7%) as an oil.

Workup

  1. customAfter completion of the reaction
  2. custommost of the methanol was evaporated under reduced pressure
  3. customThe resulting reaction mixture
  4. additionwas poured into a mixture of ice-
  5. customthe ethyl acetate layer was separated
  6. extractionThe aqueous layer was extracted with ethyl acetate (50 ml) twice
  7. dry with materialdried over anhydrous sodium sulfate
  8. customEvaporation of the ethyl acetate

Sources & evidence

ORD record
ord-ddbec8c1af6b48f9b6d29aa0b38ef018
Source dataset
uspto-grants-1996_06
Patent number
US05527952

Linked notes

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