Dimethyl Sulfate → [3-(Hydroxymethyl)-2-methoxy-5-methylphenyl]methanol

HRID 1038280

Reaktionsgleichung

Reaktionsgleichung von HRID 1038280
[OH:1][CH2:2][C:3]1[C:8]([OH:9])=[C:7]([CH2:10][OH:11])[CH:6]=[C:5]([CH3:12])[CH:4]=1.[OH-].[Na+].S(OC)(O[CH3:19])(=O)=O>O>[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH3:12])[CH:6]=[C:7]([CH2:10][OH:11])[C:8]=1[O:9][CH3:19]

Komponenten

5

Edukt 3

HCID 6497Dimethyl Sulfate3×HCID 70392,6-Dimethylol-p-cresolHCID 14798Sodium Hydroxide

Produkt 1

HCID 226768[3-(Hydroxymethyl)-2-methoxy-5-methylphenyl]methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 2,6-bis(hydroxymethyl)-p-cresol (1) (250 g, 1.48 mol), NaOH pellet (90 g, 2.25 mol) in water (2 L), dimethyl sulfate (105 g, 0.84 mol) was added slowly while stirring. The temperature of the reaction mixture was maintained below 40° C. during dimethyl sulfate addition. Copious white precipitate formed upon standing overnight, the white product (150 g) was collected by filtration as the first crop. Dimethyl sulfate (31 g, 0.25 mol) was added to the mother liquor, and the mixture was stirred at room temperature for 5 days. During this time the volume of the mother liquor was reduced to half of its original volume and 70 g of product was collected as the second crop by filtration. Total yield, 220 g (81%).

Aufarbeitung

  1. customCopious white precipitate formed
  2. filtrationthe white product (150 g) was collected by filtration as the first crop
  3. stirringthe mixture was stirred at room temperature for 5 days
  4. filtrationwas collected as the second crop by filtration

Quellen und Nachweise

ORD-Eintrag
ord-68ea383de50340b99cdf8c362fba5b8b
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08551453B2

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