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

HRID 654752

Reaction equation

HRID 654752 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-e7dd00e04394442096bec33f41038b65
Source dataset
uspto-grants-1992_07
Patent number
US05134147

Linked notes

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