4-Hydroxybenzyl Alcohol → 4-Acetoxybenzyl alcohol

HRID 39256

Reaktionsgleichung

Reaktionsgleichung von HRID 39256
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:17](Cl)(=[O:19])[CH3:18]>C(OCC)(=O)C>[C:17]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1)(=[O:19])[CH3:18]

Komponenten

5

Edukt 3

HCID 1254-Hydroxybenzyl AlcoholHCID 6367Acetyl chlorideHCID 8471Triethylamine

Produkt 1

HCID 959064-Acetoxybenzyl alcoholAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel3×

Versuchsvorschrift

To a solution of 4-hydroxybenzyl alcohol (7.5 g, 60 mmol) and 8.4 mL of triethylamine (8.4 mL, 60 mmol) in 100 mL of ethyl acetate, cooled in an ice bath, was added, via canula over 15 min, a solution of acetyl chloride (4.7 mL, 66 mmol) in 50 mL of ethyl acetate. The mixture was stirred in the same bath, which was left to come to room temperature on its own. After 18 h, the precipitate was removed by filtration. It was rinsed with 50 mL of ethyl acetate in small portions. The combined filtrates were concentrated in vacuo and purified by flash chromatography on silica gel, using 3:2 hexanes:ethyl acetate as the eluent, to afford 60 (2.853 g, 17 mmol, 29%) as an oil. 1H NMR (400 MHz, CDCl3) δ 2.31 (s, 3H), 4.69 (d, J=5.8 Hz, 2H), 7.08 (d, J=8.6 Hz, 2H), 7.38 (d, J=8.4 Hz, 2H).

Aufarbeitung

  1. additionwas added, via canula over 15 min
  2. waitwas left
  3. customto come to room temperature on its
  4. customthe precipitate was removed by filtration
  5. washIt was rinsed with 50 mL of ethyl acetate in small portions
  6. concentrationThe combined filtrates were concentrated in vacuo
  7. custompurified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-0b23a32192a74823a75b3149f61fe6ce
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524691B2

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