Potassium Carbonate → 5-Chloro-2-(3-methyl-oxetan-3-ylmethoxy)-benzaldehyde

HRID 504489Notes

Reaction equation

HRID 504489 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH3:11][C:12]1([CH2:16]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:15][O:14][CH2:13]1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][C:12]2([CH3:16])[CH2:15][O:14][CH2:13]2)=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehydeHCID 5461213(3-Methyloxetan-3-yl)methyl 4-methylbenzenesulfonate

Product 1

HCID 577501205-Chloro-2-(3-methyl-oxetan-3-ylmethoxy)-benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-chloro-2-hydroxy-benzaldehyde (4.5 g, 29 mmol), toluene-4-sulfonic acid 3-methyl-oxetan-3-ylmethyl ester in Example 13c (6.4 g, 25 mmol) and K2CO3 (8 g, 58 mmol) in anhydrous N,N-dimethylformamide (40 mL) was heated at 100° C. for 1 h. Then the mixture was filtered and the filtrate was concentrated. The residue was dissolve in EtOAc (50 mL). The solution was washed with water, dried and concentrated to give title compound as a yellow oil (5.2 g).

Workup

  1. filtrationThen the mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolve in EtOAc (50 mL)
  4. washThe solution was washed with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ea243b5c4a994b7fbcd444f2e7411c88
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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