Methylparaben → para-(pent-4-enoxy)benzoic Acid

HRID 1766634Notes

Reaction equation

HRID 1766634 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10]C)=[O:9])=[CH:6][CH:5]=1.Br[CH2:15][CH2:16][CH2:17][CH:18]=[CH2:19]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:19]([O:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)[CH2:18][CH2:17][CH:16]=[CH2:15]

Participants

6

Reactant 3

HCID 7456MethylparabenHCID 14798Sodium Hydroxide2×HCID 707041-Pentene, 5-bromo-

Product 1

HCID 2056291para-(pent-4-enoxy)benzoic AcidYield 93%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×

Procedure

2 g of sodium hydroxide, 15 ml of distilled water, 7.6 g of methyl 4-hydroxybenzoate, 0.16 g of tetrabutylammonium bromide and 5.92 ml of 5-bromopent-1-ene are successively placed in a reactor. Vigorous stirring is maintained at ambient temperature for 12 hours. After having added 30 ml of a 2.5M sodium hydroxide solution, the reaction medium is heated at 60–80° C. for 90 minutes. It is subsequently diluted with 120 ml of distilled water and extracted with two times 50 ml of diethylether. The aqueous phase is acidified with 10 ml of concentrated hydrochloric acid in order to make possible the precipitation of the acid. After filtration, washing with distilled water and then drying in a desiccator over P2O5, the acid is obtained with a yield of 93%.

Workup

  1. temperaturethe reaction medium is heated at 60–80° C. for 90 minutes
  2. extractionextracted with two times 50 ml of diethylether
  3. customthe precipitation of the acid
  4. filtrationAfter filtration
  5. washwashing with distilled water
  6. dry with materialdrying in a desiccator over P2O5
  7. customthe acid is obtained with a yield of 93%

Sources & evidence

ORD record
ord-5d8103f66cc84f20a8e6a75985bb72e6
Source dataset
uspto-grants-2007_06
Patent number
US07230123B2

Reaction notes

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