Tetrahydrofuran → 2-(3-(Benzyloxy)phenyl)-2-methylpropanal

HRID 444354Notes

Reaction equation

HRID 444354 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]([CH3:19])([CH3:18])[C:16]#N)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.[O:30]1CCCC1>CCCCCC>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]([CH3:19])([CH3:18])[CH:16]=[O:30])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 204968632-[3-(Benzyloxy)phenyl]-2-methylpropanenitrileHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 198553592-(3-(Benzyloxy)phenyl)-2-methylpropanalYield 99%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a 15° C. solution of 325 g. (1.25 mole) of 2-(3-benzyloxyphenyl)-2-methylpropionitrile in 1.85 liters of tetrahydrofuran is added 1.6 moles of diisobutylaluminum hydride as a 1.3 M solution in hexane (reaction temperature is maintained at 15°-18° C.). The reaction mixture is allowed to warm to room temperature and is stirred 2 hours longer. It is then quenched be addition to a solution of 170 ml. of concentrated sulfuric acid in 670 ml. of water (temperature ≤30° C.). The resultant mixture is allowed to warm to room temperature and is then stirred an additional 2 hours. The organic layer is separated and the aqueous phase extracted once with one liter of ether. The combined organic phase is washed with 500 ml. of water and 500 ml. of saturated sodium chloride, dried over magnesium sulfate and evaporated to yield 315 g. (99%) of the title product.

Workup

  1. customTo a 15° C.
  2. customIt is then quenched
  3. additionaddition to a solution of 170 ml
  4. customof water (temperature ≤30° C.)
  5. temperatureto warm to room temperature
  6. stirringis then stirred an additional 2 hours
  7. customThe organic layer is separated
  8. extractionthe aqueous phase extracted once with one liter of ether
  9. washThe combined organic phase is washed with 500 ml
  10. dry with materialof saturated sodium chloride, dried over magnesium sulfate
  11. customevaporated
  12. customto yield 315 g

Sources & evidence

ORD record
ord-b090ed1ca7ee4a3f96c62946b0097cb8
Source dataset
uspto-grants-1981_04
Patent number
US04263438

Reaction notes

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