Acetone → Methyl 4-octyloxybenzoate

HRID 458487Notes

Reaction equation

HRID 458487 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-octyloxybenzoateYield 86.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Into a flask were introduced methyl 4-hydroxybenzoate (251.0 g, 1.65 mol), potassium carbonate (276.37 g, 1.99 mol) and 1200 g of acetone. This was refluxed for 45 min followed by the drop-wise addition of 1-octylbromide (386.17 g, 1.99 mol) 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 pre-weighed 1L three-necked flask. The contents of the flask were subjected to high vacuum distillation to remove the excess 1-octylbromide. The pot residue gave 376 g (86% yield) of methyl 4-octoxybenzoate.

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 were subjected to high vacuum distillation
  9. customto remove the excess 1-octylbromide

Sources & evidence

ORD record
ord-259b8ea8e284400e95f723e5bbd5ada8
Source dataset
uspto-grants-2007_03
Patent number
US07192657B2

Reaction notes

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