Sulfuric Acid → 2,2'-Methylenebis(4-methyl-6-tert-butylphenol)

HRID 2058810Notes

Reaction equation

HRID 2058810 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])(C)C.S(=O)(=O)(O)O.COC[O:25][CH3:26]>>[CH2:1]([C:4]1[CH:1]=[C:5]([CH3:10])[CH:6]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:26]=1[OH:25])[C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([C:12]([CH3:13])([CH3:14])[CH3:15])[C:6]=1[OH:16]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 8020DimethoxymethaneHCID 314042,6-Di-tert-butyl-4-methylphenol

Product 1

HCID 83982,2'-Methylenebis(4-methyl-6-tert-butylphenol)Yield 84.1%

Conditions

Temperature
120 °C

Procedure

Into a reactor provided with a stirrer, thermometer and a heating bath there are charged 220 g (1 g.-mol) of 2,6-ditert.butyl-4-methylphenol, 2.2. g of concentrated sulfuric acid and the mixture is heated to the temperature of 120° C. While maintaining the temperature at 120° C., 94 g (1.24 g-mol) of methylal are fed into the reactor for 1.5 hour. On completion of the reaction, the catalyst is separated, volatile products are distilled under vacuum to give 143.0 g of 2,2'-methylene-bis(4-methyl-6-tert.butylphenol) which corresponds to 97.8% of theory as calculated for the reacted 2,6-ditert.butyl-4-methylphenol (conversion degree of the latter is 86.0%).

Workup

  1. customInto a reactor provided with a stirrer
  2. customOn completion of the reaction
  3. customthe catalyst is separated
  4. distillationvolatile products are distilled under vacuum

Sources & evidence

ORD record
ord-21e2f3b88c0f4987bf04ba3e3543ca8f
Source dataset
uspto-grants-1982_03
Patent number
US04319052

Reaction notes

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