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

HRID 487664Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 487664
[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-6bdf1f91ffb341fbb6ad00a1494f428b
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05296508

Notizen zur Reaktion

Wird geladen…