Dimethylformamide → HCID 67067122, compound

HRID 746344Notes

Reaction equation

HRID 746344 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][C:10]1(C)[CH2:13][O:12][CH2:11]1.[OH:15][C:16]1[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=1.[C:27](=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:27][CH:11]1[CH:10]([CH2:9][O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][O:15][C:16]2[CH:17]=[CH:18][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:25][CH:26]=2)[CH2:13][O:12]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8434EthylparabenHCID 11430Potassium CarbonateHCID 144346313-{[(6-Bromohexyl)oxy]methyl}-3-methyloxetane

Product 1

HCID 67067122HCID 67067122, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-[(6-bromohexyloxy)methyl]-3-methyloxetane (84 g), ethyl 4-hydroxybenzoate (50 g), potassium carbonate (50 g) and dimethyl formamide (600 mL) was stirred at 90° C. for 4 hours. Water was added to the reaction mixture to terminate the reaction and, after extraction with ethyl acetate, the liquid extract was washed with an aqueous solution of 2N-sodium hydroxide and water successively, and the organic layer was dried over anhydrous magnesium sulfate. The residues obtained by distilling off the solvent were purified on silica gel chromatography (toluene/ethyl acetate=8/2), to obtain ethyl 4-[6-(2-methyloxetane-3-ylmetoxy)hexyloxy)benzoate (85 g).

Workup

  1. customto terminate
  2. customthe reaction
  3. extractionafter extraction with ethyl acetate
  4. extractionthe liquid extract
  5. washwas washed with an aqueous solution of 2N-sodium hydroxide and water successively
  6. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  7. customThe residues obtained
  8. distillationby distilling off the solvent
  9. customwere purified on silica gel chromatography (toluene/ethyl acetate=8/2)

Sources & evidence

ORD record
ord-de40f9576c934f56ac948ce2cd1a2c83
Source dataset
uspto-grants-2008_07
Patent number
US07393569B2

Reaction notes

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