Sulfuric Acid → 2-(3-Methoxyphenyl)-2-methylpropanal

HRID 854955Notes

Reaction equation

HRID 854955 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([CH3:13])([CH3:12])[C:10]#N)[CH:6]=[CH:7][CH:8]=1.[H-].C([Al+]CC(C)C)C(C)C.[OH:24]S(O)(=O)=O>C1COCC1.CCCCCCC.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([CH3:13])([CH3:12])[CH:10]=[O:24])[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 3

HCID 1118Sulfuric AcidHCID 101301932-(3-Methoxyphenyl)-2-methylpropanenitrileHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 132969932-(3-Methoxyphenyl)-2-methylpropanal

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8900HeptaneSolvent

Procedure

To a ice cold stirred solution of 2-(3-methoxyphenyl)-2-methylpropanenitrile (27.7 g, 158 mmoles) in 250 mL of THF was added dropwise diisobutylaluminum hydride in heptane (202 mL, 1.0M solution). The mixture was allowed to warm to room temperature overnight. After cooling, a solution of concentrated H2SO4 (21.5 mL) in 85 mL of water was cautiously added in small portions. The resulting mixture was partitioned between Et2O and water, the aqueous layer further extracted, and the combined organic extracts dried over Na2SO4, filtered, and evaporated to give 2-(3-methoxyphenyl)-2-methylpropanal, 21.7 g, as an oil.

Workup

  1. temperatureAfter cooling
  2. customThe resulting mixture was partitioned between Et2O and water
  3. extractionthe aqueous layer further extracted
  4. dry with materialthe combined organic extracts dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-eacf6f42a2a24ce9a904d355680e7c5c
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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