1H-Indene-3-acetic acid → 1H-Indene-3-ethanol

HRID 260665Notes

Reaction equation

HRID 260665 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH2:16][C:17](O)=[O:18])=[CH:8]1.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C(OCC)C>[CH2:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH2:16][CH2:17][OH:18])=[CH:8]1

Participants

5

Reactant 3

HCID 30140221H-Indene-3-acetic acidHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydride

Product 1

HCID 113556481H-Indene-3-ethanolYield 73.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A suspension is prepared from 3.4 g (0.09 mol) of lithium aluminium hydride in 200 ml of dry diethyl ether. A solution of 7.7 g (0.044 mol) of 1H-indene-3-acetic acid in 150 ml of diethyl ether is added dropwise, and the mixture is stirred and heated at reflux for 20 h. The mixture is cooled, hydrolysed with approximately 8 ml of 10% aqueous sodium potassium tartrate solution, heated at boiling for 1 h and filtered. The residue is rinsed with diethyl ether, and the filtrate is evaporated under reduced pressure. The residue is purified by distillation. 5.2 g of a product are obtained which is used as it is in the following step.

Workup

  1. temperatureheated
  2. temperatureat reflux for 20 h
  3. temperatureheated
  4. filtrationfiltered
  5. washThe residue is rinsed with diethyl ether
  6. customthe filtrate is evaporated under reduced pressure
  7. distillationThe residue is purified by distillation

Sources & evidence

ORD record
ord-f3ebfdba641c490992cbe8bc9a4364a9
Source dataset
uspto-grants-1996_06
Patent number
US05530002

Reaction notes

Loading…