Ethanol → HCID 20509986, compound

HRID 1758274Notes

Reaction equation

HRID 1758274 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH:11]=[C:10]([C:12](O)=[O:13])[CH:9]=[CH:8][C:5]=2[C:6]=1[CH3:7].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O)C.O>C(OCC)C>[CH3:1][C:2]1[O:3][C:4]2[CH:11]=[C:10]([CH2:12][OH:13])[CH:9]=[CH:8][C:5]=2[C:6]=1[CH3:7]

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 962WaterHCID 20510002HCID 20510002, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20509986HCID 20509986, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2,3-Dimethylbenzofuran-6-carboxylic acid (20.0 g, 0.105 mol) was added portionwise to a stirred suspension of lithium aluminium hydride (4.0 g., 0.105 mol) in anhydrous diethyl ether (800 cm3) and the mixture was heated under reflux for 4 hr. Ethanol and water were added and the mixture was filtered. The filtrate was dried (NaSO4), filtered and the solvent was removed to give 2,3-dimethyl-6-hydroxymethylbenzofuran (18.5 g, 0.105 mol, 99.9%), m.p. 78°-79° C. (ex aqueous ethanol).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hr
  3. filtrationthe mixture was filtered
  4. dry with materialThe filtrate was dried (NaSO4)
  5. filtrationfiltered
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-8214ccfa689641649734c1fb6a7e4570
Source dataset
uspto-grants-1983_02
Patent number
US04372970

Reaction notes

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