Dimethylformamide → HCID 67067014, compound

HRID 2217105Notes

Reaction equation

HRID 2217105 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][C:10]1([CH3:14])[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(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:14][C:10]1([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][CH2:11]1

Participants

6

Reactant 4

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

Product 1

HCID 67067014HCID 67067014, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A reaction mixture comprising 84 g of 3-[(6-bromohexyloxy)methyl]-3-methyloxetane, 50 g of ethyl 4-hydroxybenzoate, 50 g of potassium carbonate and 600 ml of dimethylformamide was stirred at 90° C. for 4 hours. Water was added to the reaction mixture and the reaction was stopped. This was extracted with ethyl acetate, and the organic layer was washed with aqueous 2 N-sodium hydroxide solution and water in that order, and then dried with anhydrous magnesium sulfate. The solvent was evaporated away, and the resulting residue was purified through silica gel chromatography (elution solvent:toluene/ethyl acetate=8/2), and 85 g of ethyl 4-[6-(3-methyloxetan-3-ylmethoxy)hexyloxy]benzoate was obtained.

Workup

  1. extractionThis was extracted with ethyl acetate
  2. washthe organic layer was washed with aqueous 2 N-sodium hydroxide solution and water in that order
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customThe solvent was evaporated away
  5. customthe resulting residue was purified through silica gel chromatography (elution solvent:toluene/ethyl acetate=8/2)

Sources & evidence

ORD record
ord-a9aa2e8f83684304b2355cc1d2ebcf13
Source dataset
uspto-grants-2008_08
Patent number
US07407691B2

Reaction notes

Loading…