Methyl iodide → 2,2-Dimethyl-1H-indene-1,3(2H)-dione

HRID 1464537Notes

Reaction equation

HRID 1464537 reaction equation
[C:1]1(=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:10])C1.[CH3:12]I.[C:14](#N)[CH3:15]>>[CH3:12][C:14]1([CH3:15])[C:1](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:10]

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 6342AcetonitrileHCID 118151,3-Indandione

Product 1

HCID 5999832,2-Dimethyl-1H-indene-1,3(2H)-dione

Conditions

Temperature
60 °C

Procedure

Preparations of compounds listed in the above Table I are given below for illustrative purposes. ##STR76## 20 g (0.137 moles) of indan-1,3-dione was added to 200 ml of acetonitrile. 26 ml (0.41 moles) of methyl iodide and 8 g of a KF-celite (1:1) mixture were then added to this mixture and the resulting red mixture stirred for 18 hours at 60° C. under a nitrogen atmosphere. After cooling, the precipitate was filtered off and washed with acetonitrile. The filtrate was then evaporated to dryness and the residue chromatographically purified using a silica column with hexane/ether (6:4) as the eluent. 10.5 g of 2,2-dimethyl-indan-1,3-dione was obtained with a melting point of 107° C. ##STR77##

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate was filtered off
  3. washwashed with acetonitrile
  4. customThe filtrate was then evaporated to dryness
  5. customthe residue chromatographically purified

Sources & evidence

ORD record
ord-f192a401675045538f8bab197f74ff61
Source dataset
uspto-grants-1994_04
Patent number
US05306587

Reaction notes

Loading…