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

HRID 2292475Notes

Reaction equation

HRID 2292475 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 (2.0 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 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 (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-84f5ed5bd67344c8ac0cd2a25307af19
Source dataset
uspto-grants-1997_11
Patent number
US05683982

Reaction notes

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