1-Indanone → 1-Methyl-2,3-dihydro-1H-inden-1-OL

HRID 1656355Notes

Reaction equation

HRID 1656355 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.[CH3:11][Mg]Br>CCOCC>[OH:10][C:1]1([CH3:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 67351-IndanoneHCID 178418573HCID 178418573, compound

Product 1

HCID 5837511-Methyl-2,3-dihydro-1H-inden-1-OLYield 88%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 25.05 g (0.190 mol) of 1-indanone in 250 ml of anhydrous ether was added over 45 min to a solution of 81.0 ml (0.243 mol) of 3.0M methyl magnesium bromide in ether under N2 whilst stirring magnetically. After completion of the addition, the reaction was heated to reflux for 40 min, allowed to cool, then quenched with 30 ml of saturated ammonium chloride solution. The ether layer was decanted from a white solid, washed with water (2×100 ml), then with saturated sodium chloride solution (100 ml), dried (K2CO3) and evaporated in vacuo to leave 24.64 g (88%) of the title product as an orange oil. NMR δ(CDCl3) 1.57 (3H, s), 2.16-2.24 (2H, m), 2.77-2.89 (1H, m), 2.97-3.09 (1H, m) 7.23-7.38 (4H, m).

Workup

  1. additionAfter completion of the addition
  2. temperaturethe reaction was heated
  3. temperatureto reflux for 40 min
  4. temperatureto cool
  5. customquenched with 30 ml of saturated ammonium chloride solution
  6. customThe ether layer was decanted from a white solid
  7. washwashed with water (2×100 ml)
  8. dry with materialwith saturated sodium chloride solution (100 ml), dried (K2CO3)
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-3c374c888ae24c00b760eca5ef3095dc
Source dataset
uspto-grants-1993_10
Patent number
US05254561

Reaction notes

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