Hydrochloric Acid → HCID 22019847, compound

HRID 1080913Notes

Reaction equation

HRID 1080913 reaction equation
[C:1]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([CH2:15][CH3:16])([CH3:14])[CH3:13])[C:7]=1[OH:17])([CH2:4][CH3:5])([CH3:3])[CH3:2].[C:18]([OH:22])(=[O:21])[CH:19]=O.Cl>C(O)(=O)C>[C:12]([C:8]1[C:7](=[O:17])[C:6]([C:1]([CH2:4][CH3:5])([CH3:3])[CH3:2])=[CH:11][C:10](=[CH:19][C:18]([OH:22])=[O:21])[CH:9]=1)([CH2:15][CH3:16])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 760Glyoxylic AcidHCID 144965062,6-Di-tert-pentylphenol

Product 1

HCID 22019847HCID 22019847, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

15.0 g (0.064 Mol) of 2,6-di-tert-amylphenol and 11.4 g (0.077 mol) of 50% aqueous glyoxylic acid are dissolved in 100 ml of acetic acid. The solution is then saturated at 15°-25° C. with hydrogen chloride gas and stirred at room temperature for additional four hours. The mixture is then poured in 400 ml of ice-water and extracted with 200 ml of ethyl acetate. The ethyl acetate layer is washed several times with water, dryed over anhydrous sodium sulfate, and evaporated in vacuo. The oily residue is then chromatographed on silica gel with ethyl acetate:hexane (1:20→1:3). The pure fractions are recrystallized from hexane to give 6.5 g of the title compound as orange needles, melting at 109°-110° C.

Workup

  1. extractionextracted with 200 ml of ethyl acetate
  2. washThe ethyl acetate layer is washed several times with water
  3. customevaporated in vacuo
  4. customThe oily residue is then chromatographed on silica gel with ethyl acetate:hexane (1:20→1:3)
  5. customThe pure fractions are recrystallized from hexane

Sources & evidence

ORD record
ord-94ad8d38b49f4a1c92bd60b1fa6a08d4
Source dataset
uspto-grants-1996_12
Patent number
US05583247

Reaction notes

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