O-Cresol → 4-[[4-Hydroxy-3,5-bis(1-methylpropyl)phenyl]methyl]-2,6-dimethylphenol

HRID 64757

Reaktionsgleichung

Reaktionsgleichung von HRID 64757
[CH:1]([C:5]1[C:10]([OH:11])=[C:9]([CH:12]([CH2:14][CH3:15])[CH3:13])[CH:8]=[C:7]([CH2:16]OC)[CH:6]=1)([CH2:3][CH3:4])[CH3:2].[CH3:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[C:21]=1[OH:27].S(=O)(=O)(O)O.C1(C)C(O)=CC=CC=1>C(Cl)Cl>[OH:11][C:10]1[C:9]([CH:12]([CH3:13])[CH2:14][CH3:15])=[CH:8][C:7]([CH2:16][C:24]2[CH:23]=[C:22]([CH3:26])[C:21]([OH:27])=[C:20]([CH3:19])[CH:25]=2)=[CH:6][C:5]=1[CH:1]([CH3:2])[CH2:3][CH3:4]

Komponenten

6

Edukt 4

HCID 335O-Cresol2×HCID 1118Sulfuric AcidHCID 113352,6-DimethylphenolHCID 200694332,6-Di-sec-butyl-alpha-methoxy-p-cresol

Produkt 1

HCID 202373944-[[4-Hydroxy-3,5-bis(1-methylpropyl)phenyl]methyl]-2,6-dimethylphenolAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The procedure of Example 2 was followed using 50.45 grams (0.202 mol) of 2,6-di-sec-butyl-α-methoxy-p-cresol in 30 mL methylene chloride and 39.0 grams (0.320 mol) 2,6-dimethylphenol with 42 grams 78% sulfuric acid. The reaction was carried out at about 8° C. with mechanical stirring. The 2,6-di-sec-butylephenol used to prepare the cresol according to the procedure of Example 3 was of only 85.7 percent purity. Accordingly, the yield of the cresol was only 67% (86.9 area % by gas chromatography). The product of the invention: [4-[[4-hydroxy-3,5-bis(1-methylpropyl)phenyl]methyl]-2,6-dimethylphenol, was obtained as a viscous oil (liquid) at room temperature in 90 percent yield (61.77 grams) (84.4 area percent by gas chromatography). The compound has a pour point of 22° C. (as measured by ASTM test D-97).

Aufarbeitung

  1. customwas carried out at about 8° C. with mechanical stirring

Quellen und Nachweise

ORD-Eintrag
ord-0a22cdc07d984b8a98d59cebc4a9f378
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04609767

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