Tetrahydrofuran → 4-(1-Hydroxybutyl)benzaldehyde

HRID 732199Notes

Reaction equation

HRID 732199 reaction equation
[OH2:1].[C:2]1([CH3:12])[CH:7]=[CH:6][C:5](S(O)(=O)=O)=[CH:4][CH:3]=1.[O:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1>O>[OH:13][CH:17]([C:5]1[CH:6]=[CH:7][C:2]([CH:12]=[O:1])=[CH:3][CH:4]=1)[CH2:16][CH2:15][CH3:14]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 216964324-(1-Hydroxybutyl)benzaldehydeYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 4-(diethoxymethyl)benzaldehyde (10.4 g, 50.0 mmol) in tetrahydrofuran (200 mL) was stirred at room temperature under a nitrogen atmosphere, 2 M n-propylmagnesium bromide tetrahydrofuran solution (27.5 mL, 55.0 mmol) was added dropwise. After 30 min, aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:90-20:80) to give 1-[4-(diethoxymethyl)phenyl]butane-1-ol (6.39 g, 25.3 mmol) as a colorless oil. The oil was dissolved in a mixture of tetrahydrofuran (75 mL) and water (25 mL) and p-toluenesulfonic acid monohydrate (0.500 g, 2.63 mmol) was added. The mixture was stirred at room temperature for 5 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:90-40:60) to give the title compound (4.51 g, yield 51%, 2 step) as a colorless oil.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:90-40:60)

Sources & evidence

ORD record
ord-ee1807e8077748e482a41f17c442b116
Source dataset
uspto-grants-2009_09
Patent number
US07585880B2

Reaction notes

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