Sodium Hydroxide → 3-Ethoxy-5-methoxy-2-methyl-1H-indene

HRID 1577038Notes

Reaction equation

HRID 1577038 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH:8]([CH3:13])[C:9]2=[O:12])=[CH:5][CH:4]=1.[CH2:14](OC(OCC)OCC)[CH3:15].[OH-].[Na+]>C(O)C.CCOCC>[CH3:13][C:8]1[CH2:7][C:6]2[C:10]([C:9]=1[O:12][CH2:14][CH3:15])=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 31214Ethyl orthoformateHCID 2311786-Methoxy-2-methyl-2,3-dihydro-1H-inden-1-one

Product 1

HCID 213953003-Ethoxy-5-methoxy-2-methyl-1H-indene

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

6-Methoxy-2-methylindanone [1.76 g (0.01 mole)] is dissolved in 6.5 ml of absolute ethanol (containing 20% anhydrous ether). This solution is stirred with 2.4 g (0.016 mole) of triethylorthoformate and a drop of redistilled BF3C2H5O C2H5 for about 72 hours. The reaction mixture is diluted with ether, poured slowly into 8.1 ml of 5.0% sodium hydroxide solution with crushed ice with stirring. Two layers separate and the organic layer is washed with cold water until neutral followed by saturated sodium chloride solution and dried over sodium sulfate. This is then filtered and the solvent removed and the residue distilled with 1 ml of benzene solution which contains about 47.5 mg of anhydrous p-toluene sulfonic acid to obtain 2-methyl-3-ethoxy-5-methoxyindene.

Workup

  1. customTwo layers separate
  2. washthe organic layer is washed with cold water
  3. dry with materialdried over sodium sulfate
  4. filtrationThis is then filtered
  5. customthe solvent removed
  6. distillationthe residue distilled with 1 ml of benzene solution which

Sources & evidence

ORD record
ord-91e8b4682ef548faaf6f4b9e5eebac1b
Source dataset
uspto-grants-1976_09
Patent number
US03983253

Reaction notes

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