2,3-Dihydro-1-benzofuran-4-carboxylic acid → (2,3-Dihydro-1-benzofuran-4-yl)methanol

HRID 1602429Notes

Reaction equation

HRID 1602429 reaction equation
[O:1]1[C:5]2=[CH:6][CH:7]=[CH:8][C:9]([C:10](O)=[O:11])=[C:4]2[CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([CH2:10][OH:11])[C:4]=2[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 187874442,3-Dihydro-1-benzofuran-4-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 18787415(2,3-Dihydro-1-benzofuran-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,3-dihydrobenzofuran-4-carboxylic acid (10 g, 61 mmol) in THF (100 mL) was stirred as LAH (4.64 g, 122 mmol) was slowly added. The mixture was heated to reflux for 30 min. The mixture was cooled and quenched cautiously with ethyl acetate and then with 1N HCl (150 mL). The mixture was then made acidic with 12N HCl until all the inorganic precipitate dissolved. The organic layer was separated, and the inorganic layer was extracted twice with ethyl acetate. The organic layers were combined, washed twice with brine, and then concentrated in vacuo. This oil was Kugelrohr distilled to a clear oil that crystallized upon cooling (8.53 g, 87.6%).

Workup

  1. additionwas slowly added
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 30 min
  4. temperatureThe mixture was cooled
  5. customquenched cautiously with ethyl acetate
  6. dissolutionmade acidic with 12N HCl until all the inorganic precipitate dissolved
  7. customThe organic layer was separated
  8. extractionthe inorganic layer was extracted twice with ethyl acetate
  9. washwashed twice with brine
  10. concentrationconcentrated in vacuo
  11. distillationdistilled to a clear oil
  12. customthat crystallized
  13. temperatureupon cooling (8.53 g, 87.6%)

Sources & evidence

ORD record
ord-7a4e7ce673544ab4881d887e447fae70
Source dataset
uspto-grants-1999_11
Patent number
US05981571

Reaction notes

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