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

HRID 1831452Notes

Reaction equation

HRID 1831452 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 were successively placed in a reactor. Vigorous stirring was maintained overnight at ambient temperature. After adding 30 ml of a 2.5 M sodium hydroxide solution, the reaction medium was heated to 60–80° C. for 90 minutes. It was then diluted with 120 ml of distilled water and extracted with two times 50 ml of diethyl ether. The aqueous phase was acidified with 10 ml of concentrated hydrochloric acid to precipitate the acid. After filtering, washing with distilled water and drying in a dessicator over P2O5, the acid was obtained in a yield of 93%.

Workup

  1. temperaturethe reaction medium was heated to 60–80° C. for 90 minutes
  2. extractionextracted with two times 50 ml of diethyl ether
  3. customto precipitate the acid
  4. filtrationAfter filtering
  5. washwashing with distilled water
  6. dry with materialdrying in a dessicator over P2O5
  7. customthe acid was obtained in a yield of 93%

Sources & evidence

ORD record
ord-1adbdea5ee044662a11200ee719ae0c3
Source dataset
uspto-grants-2006_06
Patent number
US07067640B1

Reaction notes

Loading…