Methyl vinyl ketone → 2-Methoxy-2-methyl-7-t-butyl-5-isopropyl-8-propyl-chroman-6-ol

HRID 327325Notes

Reaction equation

HRID 327325 reaction equation
[CH2:1]([C:4]1[C:9]([C:10]([CH3:13])([CH3:12])[CH3:11])=[C:8]([OH:14])[C:7]([CH:15]([CH3:17])[CH3:16])=[CH:6][C:5]=1[OH:18])[CH2:2][CH3:3].[CH:19](OC)(OC)OC.[CH:26]([C:28]([CH3:30])=[O:29])=[CH2:27]>CO>[CH3:19][O:29][C:28]1([CH3:30])[CH2:26][CH2:27][C:6]2[C:5](=[C:4]([CH2:1][CH2:2][CH3:3])[C:9]([C:10]([CH3:11])([CH3:13])[CH3:12])=[C:8]([OH:14])[C:7]=2[CH:15]([CH3:17])[CH3:16])[O:18]1

Participants

5

Reactant 3

HCID 6570Methyl vinyl ketoneHCID 9005Trimethyl orthoformateHCID 540178862-Propyl-3-t-butyl-4-hydroxy-5-isopropylphenol

Product 1

HCID 542323362-Methoxy-2-methyl-7-t-butyl-5-isopropyl-8-propyl-chroman-6-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
3 °C

Procedure

Dissolve 2-propyl-3-t-butyl-4-hydroxy-5-isopropylphenol (2.0mol) and trimethyl orthoformate (0.3L) in methanol (1.2L) and degas. Place under a nitrogen atmosphere and cool to 3° C. and add concentrated sulfuric acid (5mL). Add, by dropwise addition, methyl vinyl ketone (340mL, 4.0mol) and stir without cooling for 44 hours. Pour into aqueous sodium hydrogen caronate and extract into ethyl ether. Dry (MgSO4) and evaporate the solvent in vacuo to give 2-methoxy-2-methyl-7-t-butyl-5-isopropyl-8-propyl-chroman-6-ol.

Workup

  1. customdegas
  2. additionadd concentrated sulfuric acid (5mL)
  3. temperaturewithout cooling for 44 hours
  4. extractionextract into ethyl ether
  5. dry with materialDry (MgSO4)
  6. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-5519d6f47db94e3cb941cb784bf96320
Source dataset
uspto-grants-1993_12
Patent number
US05272252

Reaction notes

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