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

HRID 54626Notes

Reaction equation

HRID 54626 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].C(=O)([O-])O.[Na+]>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

6

Reactant 4

HCID 6570Methyl vinyl ketoneHCID 9005Trimethyl orthoformateHCID 516892Sodium BicarbonateHCID 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 (2.0 mol) and trimethyl orthoformate (0.3 L) in methanol (1.2 L) and degas. Place under a nitrogen atmosphere and cool to 3° C. and add concentrated sulfuric acid (5 mL). Add, by dropwise addition, methyl vinyl ketone (340 mL, 4.0 mol) and stir without cooling for 44 hours. Pour into aqueous sodium hydrogen carbonate 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 (5 mL)
  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-e3732344467b41fbb1deba342bfdf963
Source dataset
uspto-grants-1997_04
Patent number
US05623052

Reaction notes

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