Ethanol → 2-(4-Tert-butylphenoxy)acetic acid

HRID 329773

Reaktionsgleichung

Reaktionsgleichung von HRID 329773
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(O)C.C[O-].[Na+].Br[CH2:19][C:20]([OH:22])=[O:21]>CO.Cl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:19][C:20]([OH:22])=[O:21])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

7

Edukt 4

HCID 702EthanolHCID 6227Bromoacetic AcidHCID 73934-tert-ButylphenolHCID 10942334Sodium Methoxide

Produkt 1

HCID 157182-(4-Tert-butylphenoxy)acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

4-t-butylphenol, 37.5 gm, was added to 300 ml of ethanol. 57.2 gm of a 25% solution of sodium methoxide (2 equivalents) in methanol was then added to the system. The system was stirred at room temperature for approximately 0.5 hour. Afterwards, 29.5 ml of bromoacetic acid was added and the system was then heated to reflux for 18 hours. The reaction was then stopped and the solvent removed by stripping. The resulting solid was dissolved in methylene chloride; dilute sodium hydroxide was added to give a basic pH. The resulting precipitate was dissolved in hydrochloric acid and then extracted wit methylene chloride. The methylene chloride was then stripped, and the resulting crude product air dried. Toluene was then added to the product. The toluene was removed by stripping and any remaining water was azeotroped off with the toluene to give 33.3 gm of 4-t-butylphenoxyacetic acid.

Aufarbeitung

  1. temperaturethe system was then heated
  2. temperatureto reflux for 18 hours
  3. customthe solvent removed by stripping
  4. dissolutionThe resulting solid was dissolved in methylene chloride
  5. additiondilute sodium hydroxide was added
  6. customto give a basic pH
  7. extractionextracted wit methylene chloride
  8. dry with materialthe resulting crude product air dried
  9. additionToluene was then added to the product
  10. customThe toluene was removed
  11. customany remaining water was azeotroped off with the toluene

Quellen und Nachweise

ORD-Eintrag
ord-70034e2248934fb3addf73b25dcf9ae7
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04892952

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