Sulfuric Acid → HCID 53773657, compound

HRID 851522Notes

Reaction equation

HRID 851522 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[C:5]([OH:12])=[CH:4][C:3]=1[CH2:13][C:14]([OH:16])=[O:15].S(=O)(=O)(O)O.[CH2:22]=[C:23]([CH3:25])[CH3:24]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:9])[CH3:10])[C:5]([OH:12])=[CH:4][C:3]=1[CH2:13][C:14]([O:16][C:23]([CH3:25])([CH3:24])[CH3:22])=[O:15]

Participants

5

Reactant 3

HCID 1118Sulfuric Acid2×HCID 8255IsobutyleneHCID 20501407HCID 20501407, compound

Product 1

HCID 53773657HCID 53773657, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a 200-ml four-necked flask, were charged 22.2 g of 2-methyl-4-t-butyl-5-hydroxyphenylacetic acid, 100 ml of toluene and 1 ml of concentrated sulfuric acid, and isobutene was blown into the mixture at 50° to 60° C. for a period of 3 hours. After completion of the reaction, the reaction mixture was freed from the catalyst (sulfuric acid) by washing with water and freed from the solvent under reduced pressure to obtain 26.7 g (96% yield) of yellow t-butyl 2-methyl-4-t-butyl-5-hydroxyphenylacetate, which was recrystallized from n-hexane to obtain white crystals melting at 105.0° to 106.0° C.

Workup

  1. customAfter completion of the reaction
  2. washby washing with water

Sources & evidence

ORD record
ord-8f57812f494f46d8bc35ddb363b499fb
Source dataset
uspto-grants-1983_05
Patent number
US04385143

Reaction notes

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