Water → (2,3-Dihydro-1-benzofuran-2-yl)methanol

HRID 2372747Notes

Reaction equation

HRID 2372747 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][CH:8]1[C:16](O)=[O:17].O.[OH-].[Na+]>C(OCC)C>[O:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][CH:8]1[CH2:16][OH:17]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 27765552,3-Dihydro-1-benzofuran-2-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 2795428(2,3-Dihydro-1-benzofuran-2-yl)methanolYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A three-necked flask is charged with 17 g of lithium aluminum hydride dissolved in anhydrous ethyl ether. 3 g of 2,3-dihydro-2-benzofurancarboxylic acid (Chim. Ler., (1973), 3, p. 259), dissolved in 1,140 ml of ethyl ether, are then introduced. The reaction medium is left stirring overnight. It is then hydrolyzed in an ice bath with 15.2 ml of water, 15.2 ml of 4N sodium hydroxide and then 45.2 ml of water. The complex is drained and washed with ethyl ether and the filtrate is dried and distilled to obtain the expected compound.

Workup

  1. additionare then introduced
  2. waitThe reaction medium is left
  3. washwashed with ethyl ether
  4. customthe filtrate is dried
  5. distillationdistilled

Sources & evidence

ORD record
ord-0636f161065a4f1ea476a404de57cff5
Source dataset
uspto-grants-1992_03
Patent number
US05100902

Reaction notes

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