Acetic Acid → HCID 19046537, compound

HRID 2396294Notes

Reaction equation

HRID 2396294 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=[O:3].[CH:6]([C:9]1[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[CH:12]=[C:11]([CH:18]([CH3:20])[CH3:19])[CH:10]=1)([CH3:8])[CH3:7].[C:21](O)(=[O:23])[CH3:22]>S(=O)(=O)(O)O>[C:21]([O:3][CH:2]([C:12]1[C:13]([CH:15]([CH3:17])[CH3:16])=[CH:14][C:9]([CH:6]([CH3:8])[CH3:7])=[CH:10][C:11]=1[CH:18]([CH3:20])[CH3:19])[C:1]([OH:5])=[O:4])(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 760Glyoxylic AcidHCID 128601,3,5-Triisopropylbenzene

Product 1

HCID 19046537HCID 19046537, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Glyoxylic acid (1.99 g, 27 mmol) and 1,3,5-triisopropylbenzene (5.0 g, 24.5mmol) were mixed in 30 mL glacial acetic acid and 2 mL concentrated sulfuric acid. The resulting solution was heated to reflux for 5 hours andthen stirred at room temperature for 16 hours. The reaction mixture was poured into 100 g ice and the resulting mixture was extracted with diethylether. The organic layer was dried over MgSO4, filtered, and concentrated to give an oily solid which was recrystallized from hexanes to give 3.29 g of acetyloxy[2,4,6-tris(1-methylethyl)phenyl]acetic acid, mp 166°-169° C.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 5 hours
  3. extractionthe resulting mixture was extracted with diethylether
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an oily solid which
  8. customwas recrystallized from hexanes

Sources & evidence

ORD record
ord-d4875b8bf9d640229c399a73a1307bdb
Source dataset
uspto-grants-1996_02
Patent number
US05491172

Reaction notes

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