Potassium sodium tartarate → 2-(2-Hydroxyethyl)-2,3-dihydro-1H-inden-1-ol

HRID 1731148Notes

Reaction equation

HRID 1731148 reaction equation
C([O:3][C:4](=O)[CH2:5][CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:15])C.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1COCC1>[OH:15][CH:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14][CH:6]1[CH2:5][CH2:4][OH:3]

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 111835591H-Indene-2-acetic acid, 2,3-dihydro-1-oxo-, ethyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 214953232-(2-Hydroxyethyl)-2,3-dihydro-1H-inden-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-oxoindane-2-acetic acid ethyl ester acid (5 g), described in Example 475, in dry THF (20 ml) is added to a stirred slurry of lithium aluminum hydride (3.6 g) in 120 ml of the same solvent. The reaction mixture is heated at reflux for 36 hr., allowed to cool, and decomposed with 30% aqueous solution of sodium potassium tartrate (14.4 ml). After filtration, the precipitate is washed with THF. The filtrate and washing are dried. Removal of solvent gives an oil which crystallizes from benzene to give the title compound m.p. 80°-82° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 36 hr
  3. temperatureto cool
  4. filtrationAfter filtration
  5. washthe precipitate is washed with THF
  6. washThe filtrate and washing
  7. customare dried
  8. customRemoval of solvent
  9. customgives an oil which
  10. customcrystallizes from benzene

Sources & evidence

ORD record
ord-64db10d8d98047ad869a670b152e2491
Source dataset
uspto-grants-1976_11
Patent number
US03995052

Reaction notes

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