Dimethylformamide → HCID 14370897, compound

HRID 2165334Notes

Reaction equation

HRID 2165334 reaction equation
CN([CH:4]=[O:5])C.[CH2:6]([O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26]([OH:28])=[O:27])=[CH:21][CH:20]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].Br[CH:30]([CH3:34])[C:31](O)=[O:32].[C:35](=O)([O-])[O-].[K+].[K+]>O>[CH2:6]([O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26]([O:28][CH:30]([C:31]([O:5][CH2:4][CH3:35])=[O:32])[CH3:34])=[O:27])=[CH:21][CH:20]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 117292-Bromopropionic acidHCID 10336152Benzeneacetic acid, 4-(dodecyloxy)-

Product 1

HCID 14370897HCID 14370897, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a DMF solution (30 ml) of 4-dodecyloxyphenylacetic acid (2.4 g, 7.5 mmol.) and 2-bromopropionic acid (1.5 g, 8 mmol.) was added potassium carbonate (1.5 g, 10 mmol.). The mixture was stirred at 80° C. for 2 hours. The reaction solution was cooled, to which was added water (50 ml). The mixture was subjected to extraction with IPE. The organic layer was washed with water, dried and concentrated under reduced pressure. The concentrate was purified by means of a silica gel chromatography (developing solvent: IPE) to give 1-ethoxycarbonylethyl 4-dodecyloxyphenylacetate (2-i, 2.4 g, 76%).

Workup

  1. temperatureThe reaction solution was cooled, to which
  2. extractionThe mixture was subjected to extraction with IPE
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe concentrate was purified by means of a silica gel chromatography (developing solvent: IPE)

Sources & evidence

ORD record
ord-e91a960c508948bd8dff69722ce7e319
Source dataset
uspto-grants-1990_07
Patent number
US04939274

Reaction notes

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