4-Hydroxybenzyl Alcohol → Ethyl 2-(3,5-dimethylphenoxy)acetate

HRID 630628Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 630628
[C:1](O)(=O)[CH2:2][CH2:3]C#C.O[CH2:9]C1C=CC(O)=CC=1.C1CCC(N=C=NC2CCCCC2)CC1.[C:32]([O:35][CH2:36][CH3:37])(=[O:34])[CH3:33].[CH2:38]1[CH2:42][O:41][CH2:40][CH2:39]1>>[CH3:3][C:2]1[CH:1]=[C:42]([CH:38]=[C:39]([CH3:9])[CH:40]=1)[O:41][CH2:33][C:32]([O:35][CH2:36][CH3:37])=[O:34]

Komponenten

6

Edukt 5

HCID 1254-Hydroxybenzyl AlcoholHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 10868DicyclohexylcarbodiimideHCID 224644-Pentynoic acid

Produkt 1

HCID 7018365Ethyl 2-(3,5-dimethylphenoxy)acetateAusbeute 40 %

Versuchsvorschrift

Referring to FIG. 42, a mixture of pent-4-ynoic acid (1.10 g. 11.2 mmol), 4-(hydroxymethyl)phenol (1.40 g, 11.2 mmol) and DCC (3.5 g, 16.8 mmol) in THF (30 mL) was stirred at room temperature overnight. Ethyl acetate was added to dilute the mixture and the white solid was filtered off. The filtrate was collected and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (petroleum ether/EtOAc=3:1 to 2:1) to afford compound 1 (0.91 g, 40% yield); 1H NMR (300 MHz, DMSO-d6): δ 7.35 (d, J=8.4 Hz, 2H), 7.06 (d, J=8.4 Hz, 2H), 5.23 (t, J=6.0 Hz, 1H), 4.49 (d, J=5.7 Hz, 2H), 2.90-2.89 (m, 1H), 2.81-2.76 (m, 2H), 2.55-2.50 (m, 2H).

Aufarbeitung

  1. additionto dilute the mixture
  2. filtrationthe white solid was filtered off
  3. customThe filtrate was collected
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica gel (petroleum ether/EtOAc=3:1 to 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-a1f6782e27954fb280d4e741b02bccf1
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315542B2

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