Water → 5-Chloro-2-(cyclobutylmethoxy)benzaldehyde

HRID 1604393Notes

Reaction equation

HRID 1604393 reaction equation
[Cl:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.S(O[CH2:22][CH:23]1[CH2:26][CH2:25][CH2:24]1)(C1C=CC(C)=CC=1)(=O)=O.O>CN(C=O)C.[K]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:22][CH:23]2[CH2:26][CH2:25][CH2:24]2)=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

6

Reactant 3

HCID 962WaterHCID 124815-Chloro-salicylaldehydeHCID 13163931Cyclobutylmethyl 4-methylbenzenesulfonate

Product 1

HCID 226225075-Chloro-2-(cyclobutylmethoxy)benzaldehydeYield 117.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 5462222PotassiumSolvent

Conditions

Temperature
50 °C

Procedure

5-Chlorosalicylaldehyde (7.7 g, 49.4 mmol) was dissolved in DMF (20 ml) with potassium carbonte (7.5 g, 54.1 mmol) and the cyclobutanemethanol tosylate (1 3 g, 54.1 mmol). The mixture was stirred at 50° C. under argon for 16 hours. Poured into water (500 ml). extracted with ethyl acetate (4×100 ml)and the combined organic fractions washed with 1M sodium hydroxide solution (100 ml), water (100 ml), saturated brine (100 ml) dried (MgSO4) and concentrated in vacuo to give 5-chloro-2-(cyclobutylmethoxy)benzaldehyde as a brown oil (13 g) which was used without further purification.

Workup

  1. extractionextracted with ethyl acetate (4×100 ml)
  2. washthe combined organic fractions washed with 1M sodium hydroxide solution (100 ml), water (100 ml), saturated brine (100 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0f40edc91ce04a4a96f8921c4e0a3ab2
Source dataset
uspto-grants-1999_11
Patent number
US05994353

Reaction notes

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