Water → 4-Methoxy-indan-5-carbaldehyde

HRID 389318Notes

Reaction equation

HRID 389318 reaction equation
[OH:1][C:2]1[C:10]([CH:11]=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][CH2:6]2.[C:13](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[CH3:13][O:1][C:2]1[C:10]([CH:11]=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][CH2:6]2

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 866431034-Hydroxy-2,3-dihydro-1H-indene-5-carbaldehyde

Product 1

HCID 866431044-Methoxy-indan-5-carbaldehydeYield 53.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
26.5 °C

Procedure

To a stirred suspension of 4-Hydroxy-indan-5-carbaldehyde (52.0 gm, 0.320 mole) and Potassium carbonate (57.2 gm, 0.414 mole) in Dimethylformamide (200 ml) solution of Methyl iodide (22 ml, 0.351 mole) in 60 ml Dimethylformamide was added at 0-5° C. The reaction mixture was stirred at 25-28° C. for 4 hours and then poured into water (200 ml), further it was extracted with Ethyl acetate (2×500 ml). The organic layer was dried over Sodium sulphate, distilled under vacuum to give crude product which was purified through column chromatography using Ethyl acetate:Hexane (3:97) as mobile phase. The collected fractions were distilled under vacuum to give 30 gm of desired product as a viscous oil.

Workup

  1. additionwas added at 0-5° C
  2. extractionwas extracted with Ethyl acetate (2×500 ml)
  3. dry with materialThe organic layer was dried over Sodium sulphate
  4. distillationdistilled under vacuum
  5. customto give crude product which
  6. customwas purified through column chromatography
  7. distillationThe collected fractions were distilled under vacuum

Sources & evidence

ORD record
ord-9f8ad72617ca4eb9bc34904517789f6a
Source dataset
uspto-grants-2013_02
Patent number
US08378118B2

Reaction notes

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