1-Indanone → 1-Indanol

HRID 223119

Reaction equation

HRID 223119 reaction equation
[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1>C1C=CC=CC=1.CCOCC>[CH:1]1([OH:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 67351-Indanone

Product 1

HCID 228191-IndanolYield 74.4%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
35 °C

Procedure

20 g Indanone (obtained according to Example VIII) is added to a solution of 1.5 molequivalent NaAlH2 (OC2H4OCH3)2 in a mixture of benzene and ether in the course of which the temperature raises to 35° C. Then the reaction mixture is stirred during one hour, poured out into ice and extracted with ether. The solution in ether is washed with NaCl solution, dried and evaporated. The residue is distilled under diminished pressure yielding 15.1 g indanol. B.p. 115° C./1 mm Hg. The indanol is dissolved in 100 ml cyclohexane and during 30 min. gaseous HCl is introduced followed by N2 to remove the excess of HCl. The reaction mixture is evaporated and the residue is distilled under diminished pressure yielding 12.9 g indanyl chloride. B.p. 95° C./1 mm Hg.

Workup

  1. additionpoured out into ice
  2. extractionextracted with ether
  3. washThe solution in ether is washed with NaCl solution
  4. customdried
  5. customevaporated
  6. distillationThe residue is distilled under diminished pressure

Sources & evidence

ORD record
ord-228021af54c942849e9dbb71f37de912
Source dataset
uspto-grants-1982_10
Patent number
US04352748

Linked notes

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