Hydrochloric Acid → (2-methyl-5-phenylfuran-3-yl)methanol

HRID 1877029Notes

Reaction equation

HRID 1877029 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][C:6]=1[C:7](OCC)=[O:8].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl.O>O1CCCC1>[CH3:1][C:2]1[O:3][C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][C:6]=1[CH2:7][OH:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10331426ethyl 2-methyl-5-phenyl-3-furoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 2776433(2-methyl-5-phenylfuran-3-yl)methanolYield 100.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of ethyl 2-methyl-5-phenyl-3-furancarboxylate (5.7 g) in tetrahydrofuran (30 mL) was added dropwise to a suspension of lithium aluminum hydride (1.0 g) in tetrahydrofuran (30 mL) at 0° C. and, after the completion of the dropwise addition, the mixture was stirred at 0° C. for 30 min. The reaction mixture was treated with 1N hydrochloric acid, poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (4.7 g, 100%) as an oil.

Workup

  1. additionafter the completion of the dropwise addition
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-523c8da57d794baca9819a91d1cf22ce
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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