Water → 2-(2-Hydroxyethyl)-2,3-dihydrobenzofuran

HRID 441422Notes

Reaction equation

HRID 441422 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH:2]1[CH2:10][C:11](O)=[O:12].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[OH:12][CH2:11][CH2:10][CH:2]1[CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:1]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 219494592-(2,3-Dihydro-1-benzofuran-2-yl)acetic acid

Product 1

HCID 199363482-(2-Hydroxyethyl)-2,3-dihydrobenzofuran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The starting material is prepared as follows: The solution of 14.2 g of 2-(2,3-dihydrobenzofuran-2-yl)-acetic acid [Gazz. Chim. Ital. 93, 52 (1963)] in 100 ml of tetrahydrofuran is added dropwise to the suspension of 4.55 g of lithium aluminum hydride in 200 ml of tetrahydrofuran while stirring. The mixture is refluxed for 18 hours, then cooled in an ice-bath and decomposed by adding 4.5 ml of water, 4.5 ml 15% aqueous sodium hydroxide and 14.6 ml of water. It is filtered, evaporated and the residue taken up in ethyl acetate. The solution is washed with aqueous sodium bicarbonate, water and saturated aqueous sodium chloride, dried, evaporated and the residue distilled in a kugelrohr at 140°/0.1 mmHg, to yield the 2-(2-hydroxyethyl)-2,3-dihydrobenzofuran.

Workup

  1. customThe starting material is prepared
  2. temperatureThe mixture is refluxed for 18 hours
  3. temperaturecooled in an ice-bath
  4. filtrationIt is filtered
  5. customevaporated
  6. washThe solution is washed with aqueous sodium bicarbonate, water and saturated aqueous sodium chloride
  7. customdried
  8. customevaporated
  9. distillationthe residue distilled in a kugelrohr at 140°/0.1 mmHg

Sources & evidence

ORD record
ord-0507894a0b814864af13798506c0cf24
Source dataset
uspto-grants-1977_08
Patent number
US04039676

Reaction notes

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