4-Hydroxybenzaldehyde → 4-(3,3-Dimethylbutoxy)benzaldehyde

HRID 629132Notes

Reaction equation

HRID 629132 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Cl[CH2:11][CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14].[I-].[Na+].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:14][C:13]([CH3:16])([CH3:15])[CH2:12][CH2:11][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 761111-Chloro-3,3-dimethylbutane

Product 1

HCID 102420874-(3,3-Dimethylbutoxy)benzaldehydeYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 4-hydroxybenzaldehyde (200 mg, 1.64 mmol), 1-chloro-3,3-dimethylbutane (395 mg, 1.97 mmol), sodium iodide (24 mg, 0.16 mmol), and cesium carbonate (800 mg, 2.46 mmol) in anhydrous dimethylformamide (5 mL) was stirred at 80° C. overnight. After cooling to room temperature, solids were filtered and washed with ether. The filtrate was washed with 2 N sodium hydroxide (2×20 mL), water (20 mL), and brine (20 mL), dried over magnesium sulfate, filtered, and concentrated to give 4-(3,3-dimethylbutoxyl)benzaldehyde (262 mg, 78% crude) as a pale yellow oil that was used without further purification or characterization.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationsolids were filtered
  3. washwashed with ether
  4. washThe filtrate was washed with 2 N sodium hydroxide (2×20 mL), water (20 mL), and brine (20 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-23997737ec954abd986e8cd86c56a09a
Source dataset
uspto-grants-2016_04
Patent number
US09315495B2

Reaction notes

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