Dichloromethane → Methanone, (4-methyl-2-(1-methylethoxy)phenyl)-

HRID 1777266Notes

Reaction equation

HRID 1777266 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].I[CH:13]([CH3:15])[CH3:14].C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>CN(C=O)C>[CH:13]([O:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 696002-Hydroxy-4-Methoxybenzaldehyde

Product 1

HCID 183879Methanone, (4-methyl-2-(1-methylethoxy)phenyl)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

To the solution of 2-hydroxy-4-methoxybenzaldehyde 10 (6.6 mmol, 1 equiv.) and 2-iodopropane (7.23 mmol, 1.1 equiv.) in 7 mL of DMF was added K2CO3 (26.3 mmol, 4 equiv.). The reaction was stirred at 45° C. for 18 h. Next day, added DCM 5 mL, filtered off solid, and washed solid with DCM twice. The filtrate was washed by water. And then organic layer was dried over MgSO4, and concentrated. The remaining residues was purified by Biotage SP1:0-20% EtOAc in hexane over 7 CV, 20% EtOAc in hexane over 5 CV.

Workup

  1. filtrationfiltered off solid
  2. washwashed solid with DCM twice
  3. washThe filtrate was washed by water
  4. dry with materialAnd then organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customThe remaining residues was purified by Biotage SP1

Sources & evidence

ORD record
ord-4ede17d0966f4e10baac764334541ec0
Source dataset
uspto-grants-2016_02
Patent number
US09266860B2

Reaction notes

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