Acetic Anhydride → (4-Acetoxymethyl-phenoxy)-acetic Acid Methyl Ester

HRID 1882316Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1882316
[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][OH:13])=[CH:8][CH:7]=1.[C:15](OC(=O)C)(=[O:17])[CH3:16]>N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][O:13][C:15](=[O:17])[CH3:16])=[CH:8][CH:7]=1

Komponenten

4

Edukt 2

HCID 7918Acetic AnhydrideHCID 690034Methyl 2-(4-hydroxymethylphenoxy)acetate

Produkt 1

HCID 20717763(4-Acetoxymethyl-phenoxy)-acetic Acid Methyl EsterAusbeute 61,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A solution of (4-hydroxymethyl-phenoxy)-acetic acid methyl ester 69 (100 grams, 509 mmol), acetic anhydride (250 mL) and pyridine (20 mL) was refluxed for 4 hours. Reaction mixture was poured in to ice water (1000 mL) and crude 70 was extracted into chloroform, dried over Na2SO4, and distilled. The crude was vacuum distilled to give pure 70 (75 grams, 61.7%) as a light yellow syrup, Bp15 206-210° C. The structure was confirmed with NMR. IHNMR (CDCl3) δ 2.05 (s, 3H, O═C—CH3), 3.78 (s, 3H, ester), 4.62 (s, 2H, OCH2), 5.02 (s, 2H, CH2), 6.88 (d, 2H, Ar), 7.33 (d, 2H, Ar).

Aufarbeitung

  1. customReaction mixture
  2. extractionwas extracted into chloroform
  3. dry with materialdried over Na2SO4
  4. distillationdistilled
  5. distillationdistilled

Quellen und Nachweise

ORD-Eintrag
ord-559f23ff748b4188a153ca4242680741
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318973B2

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