1-Bromooctadecane → HCID 54176565, compound

HRID 488297Notes

Reaction equation

HRID 488297 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8](O)[CH:9]=1)=[O:3].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][CH2:26][CH2:27][CH2:28][CH3:29].C(=O)([O-])[O-:31].[K+].[K+]>CN(C=O)C>[CH3:12][CH2:13][CH:14]([O:31][CH2:1][C:2]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)=[O:3])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 82181-BromooctadecaneHCID 84873-HydroxyacetophenoneHCID 11430Potassium Carbonate

Product 1

HCID 54176565HCID 54176565, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.0 g (14.7 mmol) of 3-hydroxyacetophenone, 5.9 g (17.6 mmol) of 1-bromooctadecane and 4.1 g (29.4 mmol) of anhydrous potassium carbonate in 35 ml of anhydrous DMF was stirred and heated at 80° for 45 hours. The solvent was removed under high vacuum, the residue was treated with 50 ml of 0.5 N HCl and the resultant solid was filtered and recrystallized from methanol to give 3.35 g (59% yield, mp 50°-52°) of 3-octadecyloxyacetophenone.

Workup

  1. temperatureheated at 80° for 45 hours
  2. customThe solvent was removed under high vacuum
  3. additionthe residue was treated with 50 ml of 0.5 N HCl
  4. filtrationthe resultant solid was filtered
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-ca548c56984c4a81ae017aa01b9bc12c
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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