Water → 7-Methoxy-6-methyl-indan-4-carbaldehyde

HRID 1099367Notes

Reaction equation

HRID 1099367 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:12]=[O:13])[C:5]2[CH2:6][CH2:7][CH2:8][C:9]=2[C:10]=1[OH:11].[C:14](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[CH3:14][O:11][C:10]1[C:9]2[CH2:8][CH2:7][CH2:6][C:5]=2[C:4]([CH:12]=[O:13])=[CH:3][C:2]=1[CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 230311827-Hydroxy-6-methyl-2,3-dihydro-1h-indene-4-carbaldehyde

Product 1

HCID 771748277-Methoxy-6-methyl-indan-4-carbaldehydeYield 88.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
27.5 °C

Procedure

To a stirred suspension of 6-Methyl-7-hydroxy-indan-4-carbaldehyde (5 gm, 0.0284 mole) and Potassium carbonate (4.7 gm, 0.0340 mole) in dimethyl formamide, Methyl iodide (2.2 ml, 0.0312 mole) was added at 0° C. The reaction mixture was stirred at 25-30° C. for 4 hours, then water (200 ml) was added and extracted with Ethylacetate (2×100 ml). The Ethylacetate layer was dried over Sodium sulphate and evaporated to give a crude mass which was purified by column chromatography using Ethyl acetate:Hexane (10:90) as a mobile phase. The fractions were distilled under vacuum to give 4.8 gm of desired product as viscous oil.

Workup

  1. additionwas added at 0° C
  2. extractionextracted with Ethylacetate (2×100 ml)
  3. dry with materialThe Ethylacetate layer was dried over Sodium sulphate
  4. customevaporated
  5. customto give a crude mass which
  6. customwas purified by column chromatography
  7. distillationThe fractions were distilled under vacuum

Sources & evidence

ORD record
ord-0034a70a917841e2be8d9166306325da
Source dataset
uspto-grants-2012_03
Patent number
US08143424B2

Reaction notes

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