Hydrochloric Acid → HCID 15390326, compound

HRID 1379312Notes

Reaction equation

HRID 1379312 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[CH3:16][C:17]([CH:19]=O)=[O:18].Cl>C(O)(=O)C.C1(C)C=CC=CC=1>[C:11]([C:7]1[C:6](=[O:15])[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:10][C:9](=[CH:16][C:17](=[O:18])[CH3:19])[CH:8]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 880MethylglyoxalHCID 314052,6-Di-tert-butylphenol

Product 1

HCID 15390326HCID 15390326, compoundYield 2.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

4.12 g (0.02 Mol) of 2,6-di-tert-butylphenol and 4.0 g (0.022 mol) of 40% aqueous pyruvic aldehyde are dissolved in 20 ml of acetic acid. The solution is then saturated at 15°-25° C. with hydrogen chloride gas and stirred at room temperature for additional two hours. The mixture is then diluted with 200 ml of toluene, washed several times with water, dried over anhydrous sodium sulfate, and evaporated in vacuo. The oily residue is then chromatographed on silica gel with toluene. The pure fractions are recrystallized three times from methanol to give 0.15 g of the title compound as orange needles, melting at 70°-72° C.

Workup

  1. washwashed several times with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. customevaporated in vacuo
  4. customThe oily residue is then chromatographed on silica gel with toluene
  5. customThe pure fractions are recrystallized three times from methanol

Sources & evidence

ORD record
ord-d15671a516584323bb7dbc7cbed943c2
Source dataset
uspto-grants-1997_09
Patent number
US05670692

Reaction notes

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