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

HRID 840321Notes

Reaction equation

HRID 840321 reaction equation
[Cl:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].S(O[CH2:28][CH:29]1[CH2:32][CH2:31][CH2:30]1)(C1C=CC(C)=CC=1)(=O)=O.O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:28][CH:29]2[CH2:32][CH2:31][CH2:30]2)=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehydeHCID 13163931Cyclobutylmethyl 4-methylbenzenesulfonate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

5-Chlorosalicylaldehyde (7.7 g, 49.4 mmol) was dissolved in DMF (20 ml) with potassium carbonate (7.5 g, 54.1 mmol) and the cyclobutanemethanol tosylate (13 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-8f4dbe8ea97b423dbe7b6a73693f07ae
Source dataset
uspto-grants-2002_04
Patent number
US06365603B1

Reaction notes

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