Dimethylformamide → HCID 20594801, compound

HRID 1479244Notes

Reaction equation

HRID 1479244 reaction equation
Br[CH2:2][CH2:3][CH2:4][OH:5].CN(C)C=O.[CH3:11][O:12][C:13](=[O:21])[C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[CH3:11][O:12][C:13](=[O:21])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:2][CH2:3][CH2:4][OH:5])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanol

Product 1

HCID 20594801HCID 20594801, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 250 mL flask was added 3-bromo-1-propanol (4.17 g, 0.03 mol), anhydrous dimethylformamide (40 mL), methyl-4-hydroxybenzoate (3.0 g, 0.02 mol) and potassium carbonate (4.15 g, 0.03 mol). The flask was placed in a 50° C. oil bath and stirred for 12 hours. After cooling the reaction was diluted with ethyl acetate, transferred to separatory funnel, washed with aqueous 0.1 N hydrochloric acid, water then brine. The organic layer was dried with magnesium sulfate, filtered, and concentrated under reduced pressure to give 5.14 g of crude oil. Column chromatography [silica gel; eluent hexanes-ethyl acetate (1.68:1)] provided the desired product (1.25 g, 30%) as a white powder. 1H (CDCl3) δ(ppm): 2.04-2.08 (m, 2H); 3.86-3.88 (m, 5H); 4.17 (t, 2H); 6.91 (d, 2H); 7.98 (d, 2H); 13C (CDCl3) δ(ppm): 31.89, 51.81, 59.88, 65.50, 114.06, 122.67, 131.57, 162.60, 166.84.

Workup

  1. customwas placed in a 50° C.
  2. temperatureAfter cooling the reaction
  3. customtransferred to separatory funnel
  4. washwashed with aqueous 0.1 N hydrochloric acid, water
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give 5.14 g of crude oil

Sources & evidence

ORD record
ord-e51df4275e0c4a1ba5ada5af6fdc2ad1
Source dataset
uspto-grants-2016_08
Patent number
US09408927B2

Reaction notes

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