Methanol → 2-Furanol, tetrahydro-5-phenyl-

HRID 1508656Notes

Reaction equation

HRID 1508656 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.[C:18]1([CH:24]2[O:28][C:27](=[O:29])[CH2:26][CH2:25]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CO.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1>[C:18]1([CH:24]2[O:28][CH:27]([OH:29])[CH2:26][CH2:25]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 13884gamma-Phenyl-gamma-butyrolactoneHCID 9855836Potassium sodium tartarateHCID 86583787Diisobutylaluminumhydride toluene

Product 1

HCID 111163882-Furanol, tetrahydro-5-phenyl-Yield 96.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4.1 mL of a 1.5 mol/L diisobutylaluminum hydride/toluene solution was added dropwise to a solution of 1.0 g of 5-phenyloxolane-2-one in 12 mL of toluene at −60° C., and the obtained mixture was then stirred for 30 minutes. Thereafter, 1 mL of methanol was added to the reaction mixture, and thereafter, 40 mL of a 20% potassium sodium tartrate aqueous solution was then added to the mixture at room temperature. The thus obtained mixture was stirred for 1 hour. Thereafter, the water layer was removed, and the solvent was then distilled away under reduced pressure, so as to obtain 0.98 g of 5-phenyloxolan-2-ol in the form of a colorless oily product.

Workup

  1. stirringThe thus obtained mixture was stirred for 1 hour
  2. customThereafter, the water layer was removed
  3. distillationthe solvent was then distilled away under reduced pressure

Sources & evidence

ORD record
ord-84e44d2e54fe4c8e95fb33881a977ad4
Source dataset
uspto-grants-2015_12
Patent number
US09221865B2

Reaction notes

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