Methyl vinyl ketone → 2H-1-Benzopyran-6-ol, 3,4-dihydro-2-methoxy-2,5,7,8-tetramethyl-

HRID 328840

Reaktionsgleichung

Reaktionsgleichung von HRID 328840
[CH3:1][C:2]1[C:3]([OH:11])=[C:4]([CH3:10])[C:5]([CH3:9])=[C:6]([CH:8]=1)[OH:7].C(OC)(OC)OC.C(C(C)=O)=C.[CH3:24][O:25][C:26]([CH:28]=[CH2:29])=[CH2:27].O=C(C)CCO.COC(OC)(C)C=C.COCCC(=O)C>CO>[OH:11][C:3]1[C:2]([CH3:1])=[C:8]2[C:6](=[C:5]([CH3:9])[C:4]=1[CH3:10])[O:7][C:26]([O:25][CH3:24])([CH3:27])[CH2:28][CH2:29]2

Komponenten

9

Edukt 7

HCID 6570Methyl vinyl ketoneHCID 9005Trimethyl orthoformateHCID 12785TrimethylhydroquinoneHCID 993382-Methoxy-1,3-butadieneHCID 1115094-Hydroxy-2-ButanoneHCID 1388892-Butanone, 4-methoxy-HCID 130289103,3-Dimethoxybut-1-ene

Produkt 1

HCID 1037632H-1-Benzopyran-6-ol, 3,4-dihydro-2-methoxy-2,5,7,8-tetramethyl-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

In the manner described in Example 1, 3.80 g (25 mmol) samples of trimethylhydroquinone were treated in 25 ml of methanol, 5.0 ml of trimethyl orthoformate, and 0.10 ml of 36 N aqueous H 2 SO 4 with 50 mmole portions of the following methyl vinyl ketone substitutes: (a), 2-methoxybutadiene; (b), 3-ketobutanol, (c), 3,3-dimethoxybutene (contaminated with about 20 percent 2-methoxybutadiene); and (d), 4-methoxy-2 -butanone. The reactions were monitored by tlc. Reactions (a),(c) and (d) were complete after 24 hr and were worked up and dried in the manner of Example 1 to give (±)-6-hydroxy-2-methoxy-2,5,7,8 -tetramethylchroman. In reaction (b), a>50 percent conversion to (±)-6-hydroxy-2-methoxy-2,5,7,8-tetramethylchroman was indicated by tlc.

Aufarbeitung

  1. customdried in the manner of Example 1

Quellen und Nachweise

ORD-Eintrag
ord-6e00b43b4c1243e7b2fc913f0fd7197d
Quelldatensatz
uspto-grants-1977_04
Patentnummer
US04018799

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