Sulfuric Acid → 3,4-Dimethoxy-α-(1-methylethyl)benzenemethanol

HRID 1664101Notes

Reaction equation

HRID 1664101 reaction equation
Br[CH:2]([CH3:4])[CH3:3].[Mg].[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[CH:11]=[O:12].S(=O)(=O)(O)O>C(OCC)C>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:11]([OH:12])[CH:2]([CH3:4])[CH3:3])[CH:13]=[CH:14][C:15]=1[O:16][CH3:17]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 63582-BromopropaneHCID 8419VeratraldehydeHCID 5462224Magnesium

Product 1

HCID 488983,4-Dimethoxy-α-(1-methylethyl)benzenemethanolYield 99.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

An isopropyl magnesium bromide ether solution prepared by using 5.6 g of 2-bromopropane, 0.94 g of magnesium and 30 ml of diethyl ether, was dropwise added to a mixture comprising 5.0 g of 3,4-dimethoxybenzaldehyde and 50 ml of diethyl ether, followed by a reaction for 15 hours under reflux. The reaction mixture was put into ice water, and dilute sulfuric acid was added, followed by stirring. Then, the mixture was extracted with methylene chloride, followed by washing with water. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 6.3 g of oily 1-(3′,4′-dimethoxyphenyl)-2-methylpropanol.

Workup

  1. customfollowed by a reaction for 15 hours
  2. temperatureunder reflux
  3. additionwas added
  4. extractionThen, the mixture was extracted with methylene chloride
  5. washby washing with water
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3cf8ed1fd356454e8021c1b61c4c75f2
Source dataset
uspto-grants-2011_10
Patent number
US08039420B2

Reaction notes

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