Methyl iodide → 4-methoxy-2,3-dihydro-1H-inden-1-one

HRID 603367Notes

Reaction equation

HRID 603367 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].[C:12](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[CH3:12][O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 5905474-Hydroxy-1-indanone

Product 1

HCID 45474914-methoxy-2,3-dihydro-1H-inden-1-oneYield 98.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

4-Hydroxy-1-indanone (5.0 g, 33.7 mmol) was dissolved in acetone (170 mL) and then potassium carbonate (9.0 g, 138.21 mmol) and MeI (9.6 g, 67.5 mmol) were added. The resulting suspension was heated to 50° C. and stirred for 3 days at which time the reaction mixture was concentrated under reduced pressure. The residue was partitioned between EtOAc and water. The organic phase was separated and the aqueous phase was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure to give the title compound (5.4 g, 98%) as a yellow solid. GC-MS m/z[M+H]+ 163.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customThe residue was partitioned between EtOAc and water
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted with EtOAc
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-009d53102b7f43028cf460b87ee52f45
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

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