4-Hydroxybenzyl Alcohol → Acetic acid, [4-(hydroxymethyl)phenoxy]-, ethyl ester

HRID 2107107Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2107107
[CH:1]1[C:6]([CH2:7][OH:8])=[CH:5][CH:4]=[C:3]([OH:9])[CH:2]=1.Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[OH:8][CH2:7][C:6]1[CH:5]=[CH:4][C:3]([O:9][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:2][CH:1]=1

Komponenten

7

Edukt 4

HCID 1254-Hydroxybenzyl AlcoholHCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Produkt 1

HCID 11413157Acetic acid, [4-(hydroxymethyl)phenoxy]-, ethyl esterAusbeute 63,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 2.00 g of p-hydroxybenzyl alcohol, 3.23 g of ethyl bromoacetate, 2.45 g of anhydrous potassium carbonate and 15 ml of N,N-dimethylformamide was added tetra-n-butylammonium bromide in a catalytic amount. The mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with ethyl acetate and insoluble matters were filtered off. The filtrate was washed with an aqueous sodium hydroxide solution and water, in this sequence. After drying over anhydrous magnesium sulfate, the solvent was distilled off. The residue was applied to silica gel column chromatography. Elution with a solvent mixture of hexane-ethyl acetate (3:2) gave 2.16 g of oily ethyl [p-(hydroxymethyl)phenoxy]acetate.

Aufarbeitung

  1. filtrationwere filtered off
  2. washThe filtrate was washed with an aqueous sodium hydroxide solution and water, in this sequence
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. washElution
  6. additionwith a solvent mixture of hexane-ethyl acetate (3:2)

Quellen und Nachweise

ORD-Eintrag
ord-4a3048df2968494ba5819b8b8a32ccd3
Quelldatensatz
uspto-grants-1990_06
Patentnummer
US04933348

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