Potassium Carbonate → HCID 86722747, compound

HRID 1525803Notes

Reaction equation

HRID 1525803 reaction equation
O[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C(=O)([O-])[O-:28].[K+].[K+]>C(#N)C.C(OC(=O)C)C>[CH2:12]([O:28][C:10]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:3](=[O:4])[CH3:2])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 123941-BromopentadecaneHCID 68490alpha-Hydroxyacetophenone

Product 1

HCID 86722747HCID 86722747, compoundYield 81.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

In acetonitrile (50 mL), 2-hydroxyacetophenone (3.9 g) and 1-bromopentadecane (8.4 g) were dissolved. Potassium carbonate (7.9 g) was added thereto and refluxed with heating for 48 hours. After cooling the reaction solution, it was diluted with ethylacetate and filtered with Celite (brand name). The filtrate was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→90:10). To the obtained solid, methanol was added, filtrated and dried under reduced pressure to obtain the title compound (8.1 g) having the following physical property values.

Workup

  1. temperaturerefluxed
  2. temperaturewith heating for 48 hours
  3. temperatureAfter cooling the reaction solution, it
  4. filtrationfiltered with Celite (brand name)
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→90:10)
  7. additionTo the obtained solid, methanol was added
  8. filtrationfiltrated
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-1b7d1e56a67845349443894d59703e60
Source dataset
uspto-grants-2015_07
Patent number
US09085523B2

Reaction notes

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