Water → 2-benzoyloxymethylene-6-methoxy-1-Tetralone

HRID 1590706Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1590706
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:10][CH:11]=[C:12]1[CH2:21][CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[CH:18]=2)[C:13]1=[O:24].O>N1C=CC=CC=1>[C:1]([O:10][CH:11]=[C:12]1[CH2:21][CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[CH:18]=2)[C:13]1=[O:24])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 7412Benzoyl chlorideHCID 2643163,4-Dihydro-2-(hydroxymethylene)-6-methoxy-1(2H)-naphthalenone

Produkt 1

HCID 538779652-benzoyloxymethylene-6-methoxy-1-TetraloneAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Benzoyl chloride (11.4 ml, 0.1 mole) was added to a stirred solution of 2-hydroxymethylene-6-methoxy-1-tetralone 2 (10 g, 0.05 mole) in about 60 mL of pyridine at about 0°. After the addition was complete, the mixture was stirred at about 23° for about 2 hours then poured into water. The solid was filtered and washed with water. The pure product was obtained by recrystallization from methanol to yield 2-benzoyloxymethylene-6-methoxy-1-Tetralone (12.1 g, 0.04 mole, 80% yield), mp 128.5°-129.5°, [Lit. Kieboom et al., Synthesis, 476-478, (1970), mp 130°-130.5°].

Aufarbeitung

  1. additionAfter the addition
  2. filtrationThe solid was filtered
  3. washwashed with water
  4. customThe pure product was obtained by recrystallization from methanol
  5. customto yield

Quellen und Nachweise

ORD-Eintrag
ord-541cd0a74e9749bab3b15925d858ae3b
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05204373

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