Acetic Acid → HCID 15295493, compound

HRID 2399910Notes

Reaction equation

HRID 2399910 reaction equation
[Li+].[OH-].C([O:16][CH2:17][C:18]1[C:22]([OH:24])([CH3:23])[O:21][C:20](=[O:25])[C:19]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=O)CCCCCCCCCCC.C(O)(=O)C>C1COCC1>[OH:16][CH2:17][C:18]1[C:22]([OH:24])([CH3:23])[O:21][C:20](=[O:25])[C:19]=1[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 9865844HCID 9865844, compound2×

Product 1

HCID 15295493HCID 15295493, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiOH (0.5M, 19.7 mL, 9.83 mmol) was added to a solution of 4-dodecoyloxymethyl-5-hydroxy-5-methyl-3-phenyl-2-furanone (Compound 5, see improved process for preparation below), in THF (20 mL) at room temperature. After stirring for 3 hours the reaction was quenched with glacial acetic acid (590 mg, 9.83 mmol) and the THF was removed by rotary evaporator. Solids were removed from the residual aqueous slurry. The clear aqueous solution containing the crude product was lyophylized, adhered to silica with methanol and purified by flash chromatography using 60% ethyl acetate/hexane to give the title alcohol.

Workup

  1. customthe THF was removed by rotary evaporator
  2. customSolids were removed from the residual aqueous slurry
  3. additionThe clear aqueous solution containing the crude product
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-a8c6e26aa1f64955987fc2d1114dd602
Source dataset
uspto-grants-1995_09
Patent number
US05451686

Reaction notes

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