Hydrochloric Acid → (2,3-Dihydro-1-benzofuran-5-yl)methanol

HRID 7422Notes

Reaction equation

HRID 7422 reaction equation
[O:1]1[CH2:5][CH2:4][C:3]2[CH:6]=[C:7]([C:10](O)=[O:11])[CH:8]=[CH:9][C:2]1=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].CO.Cl>O1CCCC1>[O:1]1[CH2:5][CH2:4][C:3]2[CH:6]=[C:7]([CH2:10][OH:11])[CH:8]=[CH:9][C:2]1=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6765832,3-Dihydrobenzo(b)furan-5-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 2776158(2,3-Dihydro-1-benzofuran-5-yl)methanolYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2,3-dihydrobenzo[b]furan-5-carboxylic acid (1.64 g, 10 mmol) in tetrahydrofuran (10 mL) was added under ice-cooling lithium aluminum hydride (949 mg, 25 mmol) and the mixture was stirred at 60° C. for 1 h. The reaction mixture was stirred under ice-cooling and methanol and 1N hydrochloric acid were added. The precipitate was filtered off and the mother liquor was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give an almost pure title compound (1.5 g, 100%).

Workup

  1. stirringThe reaction mixture was stirred under ice-
  2. temperaturecooling
  3. filtrationThe precipitate was filtered off
  4. washthe mother liquor was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-2d6bc2f5413f417781b69375e7336008
Source dataset
uspto-grants-2006_08
Patent number
US07087597B1

Reaction notes

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