1-Propanol → 8-Tert-butyl-1,3,4,5-tetrahydro-2-benzoxepine

HRID 260263Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 260263
C(O)CC.[C:5]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][O:18][CH2:19]OC)=[CH:11][CH:10]=1)([CH3:8])([CH3:7])[CH3:6].COCOC.COCOCOC>ClCCl>[C:5]([C:9]1[CH:14]=[CH:13][C:12]2[CH2:15][CH2:16][CH2:17][O:18][CH2:19][C:11]=2[CH:10]=1)([CH3:8])([CH3:7])[CH3:6]

Komponenten

6

Edukt 4

HCID 10311-PropanolHCID 8020Dimethoxymethane2×HCID 12362Bis(methoxymethyl)ether2×HCID 152718851-Tert-butyl-4-(3-methoxymethoxypropyl)benzene

Produkt 1

HCID 152718948-Tert-butyl-1,3,4,5-tetrahydro-2-benzoxepineAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The above-mentioned propanol was then converted into 1-tert-butyl-4-(3-methoxymethoxypropyl)benzene by means of dimethoxymethane, in an analogous manner to that described by J. L. Gras et al. in Synthesis 74, (1985), but using 12 equivalents of dimethoxymethane for 1 equivalent of alcohol. The above-mentioned methoxymethylether was then transformed as described by A. Rieche et al., Chem. Ber. 95, 91 (1962) but using dichloromethane as solvent. The concentration of methoxymethylether in this solvent varied between 0.1 and 0.3 M. The reaction product was purified by chromatography to provide 8-tert-butyl-1,3,4,5-tetrahydro-2-benzoxepine (yield 67%, purety>99%).

Aufarbeitung

  1. customGras et al. in Synthesis 74, (1985),
  2. customThe reaction product was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ce2003d8cdd945edaebca872af7889cb
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05527769

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