Acetic Acid → HCID 19385050, compound

HRID 2399907Notes

Reaction equation

HRID 2399907 reaction equation
[Li+].[OH-].C([O:6][CH:7]([C:20]1[C:24]([OH:26])([CH3:25])[O:23][C:22](=[O:27])[CH:21]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])(=O)C.C(O)(=O)C>C1COCC1>[OH:6][CH:7]([C:20]1[C:24]([OH:26])([CH3:25])[O:23][C:22](=[O:27])[CH:21]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 9841543HCID 9841543, compound

Product 1

HCID 19385050HCID 19385050, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiOH (0.5M, 22.6 mL, 11.32 mmol) was added to a solution of 4-(1-acetoxytridecyl)-5-hydroxy-5-methyl-2-furanone (1.00 g, 2.83 mmol) in THF (15 mL). After stirring for 3 hours at room temperature the reaction was quenched with glacial acetic acid (680 mg, 11.3 mmol) and extracted with ethylacetate. The combined organic fractions were washed with a saturated solution of aqueous sodium bicarbonate, H2O and brine. Evaporation of the dried (magnesium sulfate) extracts gave an oil which was purified by flash chromatography on silica using 40% ethyl acetate/hexane to give the title alcohol.

Workup

  1. extractionextracted with ethylacetate
  2. washThe combined organic fractions were washed with a saturated solution of aqueous sodium bicarbonate, H2O and brine
  3. customEvaporation of the
  4. dry with materialdried (magnesium sulfate)
  5. customextracts gave an oil which
  6. customwas purified by flash chromatography on silica using 40% ethyl acetate/hexane

Sources & evidence

ORD record
ord-6537c491c2454587971681896327fa12
Source dataset
uspto-grants-1995_09
Patent number
US05451686

Reaction notes

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