Ethanol → HCID 67575852, compound

HRID 1195620Notes

Reaction equation

HRID 1195620 reaction equation
[CH3:1][C:2]1([CH3:8])[C:6](=[O:7])[CH2:5][CH2:4][O:3]1.[H-].[Na+].[CH2:11]([OH:13])C.C(OCC)=O>CCOCC.O>[OH:13][CH:11]=[C:5]1[CH2:4][O:3][C:2]([CH3:8])([CH3:1])[C:6]1=[O:7]

Participants

8

Reactant 4

HCID 702EthanolHCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 130102942,2-Dimethyloxolan-3-one

Product 1

HCID 67575852HCID 67575852, compoundYield 43%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

An ether solution of dihydro-2,2-dimethyl-3-(2H)-furanone; (4.55 g, 39.9 mmol) in -30 mL of ether was added dropwise to a suspension of sodium hydride (3.2 g of 60%, 80 mmol) in 150 mL of ether containing three drops of ethanol and 6.5 mL (80 mmol) of ethyl formate stirred at 0° C. After stirring overnight at room temperature, the reaction mixture was taken up into water, the ether layer separated, washed with additional ether, acidified with 6N HCl and extracted into ether. The combined ether layers were washed with water and brine, dried over MgSO4, decolorized with charcoal, filtered and evaporated to leave 2.4 g of 4-hydroxymethylene-dihydro-2,2-dimethyl-3(2H)furanone as a colorless oil (43%).

Workup

  1. stirringAfter stirring overnight at room temperature
  2. customthe ether layer separated
  3. washwashed with additional ether
  4. extractionextracted into ether
  5. washThe combined ether layers were washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-6e298a3623ab406cad4bdfa9caace081
Source dataset
uspto-grants-1992_05
Patent number
US05112594

Reaction notes

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