Acetic Acid → HCID 19046537, compound

HRID 1781488Notes

Reaction equation

HRID 1781488 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-triiso-propylbenzene (5.0 g, 24.5 mmol) were mixed in 30 mL glacial acetic acid and 2 mL concentrated sulfuric acid. The resulting solution was heated to reflux for 5 hours and then stirred at room temperature for 16 hours. The reaction mixture was poured into 100 g ice and the resulting mixture was extracted with diethyl ether. 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 diethyl ether
  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-983d29117b79435da886a62cf097c7b9
Source dataset
uspto-grants-1997_05
Patent number
US05633287

Reaction notes

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