Potassium Carbonate → HCID 44072825, compound

HRID 1503452Notes

Reaction equation

HRID 1503452 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1.[OH:11][C:12]1[CH:20]=[C:19]2[C:15]([CH2:16][CH2:17][C:18]2=[O:21])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][O:11][C:12]2[CH:20]=[C:19]3[C:15]([CH2:16][CH2:17][C:18]3=[O:21])=[CH:14][CH:13]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 70206596-Hydroxy-1-indanone

Product 1

HCID 44072825HCID 44072825, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-methoxybenzylchloride (9.19 mL, 67.5 mmol) was added to a mixture of 6-hydroxy-1-indanone (10 g, 67.5 mmol) and potassium carbonate (14 g, 101 mmol) in 15 mL DMF. The mixture was reacted at RT for 14 h. The reaction mixture was diluted with water and extracted with DCM. The organic layer was separated and the solvents were removed by evaporation. The residue was dissolved in DCM and filtered through a plug of activated basic alumina. 6-(4-Methoxy-benzyloxy)-indan-1-one (18 g, 99%) was obtained after evaporation of the filtrate. The material was taken to the next step without further purification.

Workup

  1. customThe mixture was reacted at RT for 14 h
  2. extractionextracted with DCM
  3. customThe organic layer was separated
  4. customthe solvents were removed by evaporation
  5. dissolutionThe residue was dissolved in DCM
  6. filtrationfiltered through a plug of activated basic alumina

Sources & evidence

ORD record
ord-96bf33ebf4a042bd8b575de4fd71fdf7
Source dataset
uspto-grants-2015_12
Patent number
US09212153B2

Reaction notes

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