Water → 4-Methoxy-5-methyl-indan-1-one

HRID 389319Notes

Reaction equation

HRID 389319 reaction equation
[OH:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:12].[C:13](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O.O>CN(C)C=O>[CH3:13][O:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 668122914-Hydroxy-5-methyl-2,3-dihydro-1H-inden-1-one

Product 1

HCID 552973254-Methoxy-5-methyl-indan-1-oneYield 82.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
62.5 °C

Procedure

To a suspension of 4-Hydroxy-5-methyl-indan-1-one (50.0 gm, 0.308 mole) and Potassium carbonate (127.0 gm, 0.928 mole) in Dimethylformamide (250 ml), Dimethyl sulphate (90 ml, 0.928 mole) was added at 0° C. The reaction mixture was heated at 60-65° C. and stirred for 16 hours. The reaction mixture was poured into water (1 liter) and extracted with Ethylacetate (3×250 ml). The organic layer was dried over Sodium sulphate and distilled under vacuum to give 10.0 gm of crude product which was purified by column chromatography using Hexane as a mobile phase. The collected fractions were distilled under vacuum to give 45.0 gm of desired product as a viscous oil.

Workup

  1. additionwas added at 0° C
  2. extractionextracted with Ethylacetate (3×250 ml)
  3. dry with materialThe organic layer was dried over Sodium sulphate
  4. distillationdistilled under vacuum
  5. customto give 10.0 gm of crude product which
  6. customwas purified by column chromatography
  7. distillationThe collected fractions were distilled under vacuum

Sources & evidence

ORD record
ord-2ef6e310826c44b299876b546698b227
Source dataset
uspto-grants-2013_02
Patent number
US08378118B2

Reaction notes

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