Methyl iodide → HCID 71093185, compound

HRID 332664Notes

Reaction equation

HRID 332664 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:28]=[C:29]([OH:31])[CH:30]=1)[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].[C:32](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O.O>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:28]=[C:29]([O:31][CH3:32])[CH:30]=1)[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 71093150HCID 71093150, compound

Product 1

HCID 71093185HCID 71093185, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To an ice-cooled solution of benzyl 3-((8-(1,3-dioxolan-2-yl)octyl)oxy)-5-hydroxybenzoate (1.94 g, 4.53 mmol) in dimethyl formamide (25 mL), was added potassium carbonate (0.93 g, 6.75 mmol) followed by iodomethane (0.42 mL, 6.75 mmol). The reaction mixture was allowed to warm to room temperature over 16 hours and stood at room temperature for 3 days. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic extracts were washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure to afford the title compound (1.76 g, 88%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-05a97f8776644d76a55cd0e6313006af
Source dataset
uspto-grants-2014_11
Patent number
US08877774B2

Reaction notes

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