Sulfuric Acid → HCID 20501407, compound

HRID 851518Notes

Reaction equation

HRID 851518 reaction equation
[CH3:1][C:2]1[C:7]([CH2:8][C:9]([OH:11])=[O:10])=[C:6](C(C)(C)C)[C:5]([OH:16])=[C:4]([C:17]([CH3:20])([CH3:19])[CH3:18])[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:17]([CH3:20])([CH3:18])[CH3:19])[C:5]([OH:16])=[CH:6][C:7]=1[CH2:8][C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 12293086HCID 12293086, compound

Product 1

HCID 20501407HCID 20501407, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a 300-ml four-necked flask, were charged 27.8 g of 6-methyl-2,4-di-t-butyl-3-hydroxyphenylacetic acid, 150 ml of toluene and 3 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, then dehydrated and freed from the solvent under reduced pressure to obtain 21.5 g (97% yield) of pale yellow 2-methyl-4-t-butyl-5-hydroxyphenylacetic acid which was recrystallized from a chloroform-hexane mixture to yield white crystals melting at 132° to 134° 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-f2195535889d41dd81e117d45b540e9e
Source dataset
uspto-grants-1983_05
Patent number
US04385143

Reaction notes

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