Acetone → Methyl 4-octyloxybenzoate

HRID 2118362Notes

Reaction equation

HRID 2118362 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CC(C)=O.[CH2:22](Br)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>C(OCC)(=O)C>[CH2:22]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 180AcetoneHCID 7456MethylparabenHCID 81401-BromooctaneHCID 11430Potassium Carbonate

Product 1

HCID 2736917Methyl 4-octyloxybenzoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Into a flask was introduced 251.0 g (1.65 mol) of methyl 4-hydroxybenzoate, 276.37 g (1.99 mol) potassium carbonate and 1200 g of acetone. This was refluxed for 45 min followed by the dropwise addition of 386.17 g (1.99 mol) of 1-octylbromide over a 1 hour period. The reaction mixture was refluxed for two days. Filtration of the cooled reaction mixture and evaporation of the filtrate gave an oil. This was taken up in ethyl acetate and extracted with 5% NaOH (2×100 ml) followed by water (2×100 ml). The organic layer was dried (MgSO4), concentrated, and transferred to a 1 L three necked flask. The contents of the flask was subjected to high vacuum distillation to remove the excess 1-octylbromide. The pot residue was essentially pure methyl 4-octoxybenzoate (376 g, 86%).

Workup

  1. temperatureThis was refluxed for 45 min
  2. temperatureThe reaction mixture was refluxed for two days
  3. filtrationFiltration of the cooled reaction mixture and evaporation of the filtrate
  4. customgave an oil
  5. extractionextracted with 5% NaOH (2×100 ml)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. concentrationconcentrated
  8. distillationThe contents of the flask was subjected to high vacuum distillation
  9. customto remove the excess 1-octylbromide

Sources & evidence

ORD record
ord-0764d6fac5434d0cb410ab9e22a39fa7
Source dataset
uspto-grants-2008_10
Patent number
US07442760B2

Reaction notes

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