Methanol → 4-Hydroxy-5,5-dimethyl-2(5H)-furanone

HRID 383481Notes

Reaction equation

HRID 383481 reaction equation
[CH3:1][C:2]1([CH3:13])[O:6][C:5](=[O:7])[CH:4]=[C:3]1N1CCCC1.C[OH:15]>Cl>[OH:15][C:3]1[C:2]([CH3:13])([CH3:1])[O:6][C:5](=[O:7])[CH:4]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 252473365,5-dimethyl-4-(pyrrolidin-1-yl)furan-2(5H)-one

Product 1

HCID 547201394-Hydroxy-5,5-dimethyl-2(5H)-furanone

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
88 °C

Procedure

A suspension of 5,5-dimethyl-4-pyrrolidin-1-ylfuran-2(5H)-one (535 mg) in a mixture of MeOH (2 mL) and 5M HCl (8 mL) was heated at 88° C. for 2 hours. The mixture was cooled to room temp., extracted with CHCl3 (10×15 mL), combined, dried over Na2SO4, and evaporated to dryness to give 4-hydroxy-5,5-dimethyl-5H-furan-2-one as light brown solid. Yield: 359 mg, 95%.

Workup

  1. temperatureThe mixture was cooled to room temp.
  2. extractionextracted with CHCl3 (10×15 mL)
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-78b0883288cf4de68deadf6efa90fd01
Source dataset
uspto-grants-2013_02
Patent number
US08367664B2

Reaction notes

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