4-Hydroxybenzaldehyde → 4-Isobutoxybenzaldehyde

HRID 2248541Notes

Reaction equation

HRID 2248541 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[OH-].[K+].I[CH2:13][CH:14]([CH3:16])[CH3:15].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.CCOCC>[CH3:13][CH:14]([CH3:16])[CH2:15][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 10340Sodium CarbonateHCID 10556Isobutyl iodideHCID 14797Potassium Hydroxide

Product 1

HCID 2498104-IsobutoxybenzaldehydeYield 46%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A 1000 mL, 1 neck, round-bottomed flask equipped with a magnetic stirrer and reflux condenser is charged with 4-hydroxybenzaldehyde (33.18 g, 0.272 mol), 100 ml of ethanol, and a solution of potassium hydroxide (20.42 g, 0.309 mol) in 100 mL of ethanol. The reaction mixture is heated with stirring for one-half hour. Next 1-iodo-2-methylpropane (100 g, 0.543 mol) is added and the mixture refluxed for 12 hours. After cooling, the solvents are removed by rotary evaporation to yield a brown solid which is added to a separatory funnel containing 500 mL ether and 500 mL of 5% aqueous sodium carbonate. The layers are separated and the aqueous phase is washed with ether (2×500 mL). The combined ether layers are washed with pH 12 sodium hydroxide solution (5×200 mL) until the washes are colorless. The organic solution is then washed with brine (100 mL) and dried over magnesium sulfate. After filtration and removal of the solvents by rotary evaporation, a viscous yellow liquid is obtained. This material is purified by Kugel-Rohr distillation to give 22.3 g (0.125 mol, 46%) of a colorless liquid.

Workup

  1. customA 1000 mL, 1 neck, round-bottomed flask equipped with a magnetic stirrer
  2. temperaturereflux condenser
  3. temperatureThe reaction mixture is heated
  4. temperaturethe mixture refluxed for 12 hours
  5. temperatureAfter cooling
  6. customthe solvents are removed by rotary evaporation
  7. customto yield a brown solid which
  8. additionis added to a separatory funnel
  9. customThe layers are separated
  10. washthe aqueous phase is washed with ether (2×500 mL)
  11. washThe combined ether layers are washed with pH 12 sodium hydroxide solution (5×200 mL) until the washes
  12. washThe organic solution is then washed with brine (100 mL)
  13. dry with materialdried over magnesium sulfate
  14. filtrationAfter filtration and removal of the solvents
  15. customby rotary evaporation
  16. customa viscous yellow liquid is obtained
  17. distillationThis material is purified by Kugel-Rohr distillation

Sources & evidence

ORD record
ord-c5584e49b5ba40a691366c9e81cbc6c2
Source dataset
uspto-grants-1991_08
Patent number
US05041282

Reaction notes

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