Sulfuric Acid → HCID 20501412, compound

HRID 851519Notes

Reaction equation

HRID 851519 reaction equation
[CH3:1][C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:6](C(C)(C)C)[C:5]([OH:17])=[C:4]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:3]=1.S(=O)(=O)(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]([C:18]([CH3:21])([CH3:19])[CH3:20])[C:5]([OH:17])=[CH:6][C:7]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 53844051HCID 53844051, compound

Product 1

HCID 20501412HCID 20501412, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a 1-liter four-necked flask, were charged 58.4 g of methyl 6-methyl-2,4-di-t-butyl-3-hydroxyphenylacetate, 400 ml of toluene, and 6 ml of concentrated sulfuric acid. The mixture was heated under reflux for about 5 hours under a nitrogen stream. After completion of the reaction, the reaction mixture was neutralized with an aqueous sodium carbonate solution, washed with water, dehydrated, and freed from the solvent under reduced pressure to obtain 46.2 g (98% yield) of pale yellow methyl 2-methyl-4-t-butyl-5-hydroxyphenylacetate which was distilled under reduced pressure (1 mmHg, 130°-140° C.) or recrystallized from n-hexane to yield white crystals having a melting point of 100.0°-101.5° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for about 5 hours under a nitrogen stream
  3. customAfter completion of the reaction
  4. washwashed with water

Sources & evidence

ORD record
ord-f1aa382d302d44648be06d5c28d0f10a
Source dataset
uspto-grants-1983_05
Patent number
US04385143

Reaction notes

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