Chloroacetic Acid → 2-(4-Tert-butylphenoxy)acetic acid

HRID 5005

Reaktionsgleichung

Reaktionsgleichung von HRID 5005
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[O-]C1C=CC=CC=1.Cl[CH2:22][C:23]([OH:25])=[O:24].Cl>CN(C)C=O.C(OCC)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:22][C:23]([OH:25])=[O:24])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

8

Edukt 5

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 73934-tert-ButylphenolHCID 24758Sodium hydrideHCID 119047Phenolate

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

A solution of 10.0 g (66.7 mmoles) p-tertbutylphenol in 50 ml dry dimethyl formamide was added, dropwise, to a mechanically stirred slurry of 8.4 g sodium hydride (as 50% oil dispersion) in 500 ml dry dimethyl formamide. To the phenoxide solution was added, dropwise, a solution of 6.3 g (66.3 mmoles) chloroacetic acid in 50 ml dry dimethyl formamide. The reaction mixture was stirred at room temperature for two hours. The reaction mixture was diluted with 200 ml diethyl ether and acidified with 3N hydrochloric acid. The aqueous layer was removed and washed with 200 ml diethyl ether. The organic layers were combined, dried (MgSO4) and evaporated to a white gummy residue which was dried in vacuo yielding p-t-butylphenoxyacetic acid, 9.0 g (65%).

Aufarbeitung

  1. customThe aqueous layer was removed
  2. washwashed with 200 ml diethyl ether
  3. dry with materialdried (MgSO4)
  4. customevaporated to a white gummy residue which
  5. customwas dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-078c67ca02f34b0ebcf180a005a5ee53
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05242936

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