Formaldehyde → 5,8-dimethyl-6-(1,1-dimethylethyl)-4H-1,3-benzodioxin

HRID 1638506Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1638506
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[C:5]([CH3:12])=[CH:4][C:3]=1[OH:13].C=O.S(=O)(=O)(O)O.[O:21]1[CH2:26]COC[CH2:22]1>>[CH3:12][C:5]1[C:4]2[CH2:26][O:21][CH2:22][O:13][C:3]=2[C:2]([CH3:1])=[CH:7][C:6]=1[C:8]([CH3:9])([CH3:10])[CH3:11]

Komponenten

5

Edukt 4

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 312751,4-DioxaneHCID 87249Phenol, 4-(1,1-dimethylethyl)-2,5-dimethyl-

Produkt 1

HCID 146183785,8-dimethyl-6-(1,1-dimethylethyl)-4H-1,3-benzodioxinAusbeute 59 %

Versuchsvorschrift

Reaction of 2,5-dimethyl-4-(1,1-dimethylethyl)-phenol (20.2 g, GLC purity 88%, 0.1 mol, which may be prepared as described by W. Weinrich, Ind. Eng. Chem. (1943) 35, 264-272), 40% formaldehyde solution (80 mL, 1.07 mol), p-dioxane (170 mL) and sulfuric acid (10 mL) according to the procedure described in Example 2, provided after distillation 13.05 g (59% yield, GLC purity 97%) of 5,8-dimethyl-6-(1,1-dimethylethyl)-4H-1,3-benzodioxin, bp 139° C., 3 mm; 1H-NMR (CDCl3)δ 1.40 (9H, s), 2.21 (6H, s), 4.79 (2H, s), 5.14 (2H, s); 7.01 (1H, s); IR (film)νmax 2940, 1580, 1475 cm-1 ; MS m/e 220, 205, 190, 185, 147; UVλmax (ethanol) 225 nm (ε=4270), 281 nm (ε=1490).

Aufarbeitung

  1. customprovided

Quellen und Nachweise

ORD-Eintrag
ord-67732a2afcf1469fa7ed5b87f649ccc3
Quelldatensatz
uspto-grants-1989_11
Patentnummer
US04880775

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