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

HRID 1038280

Reaction equation

HRID 1038280 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-68ea383de50340b99cdf8c362fba5b8b
Source dataset
uspto-grants-2013_10
Patent number
US08551453B2

Linked notes

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