Potassium Carbonate → p-Toluenesulfonate

HRID 1809807Notes

Reaction equation

HRID 1809807 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH3:17][O:18][CH2:19][CH2:20][CH2:21][O:22][S:23]([C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1)(=[O:25])=[O:24]>CN(C=O)C>[CH3:17][O:18][CH2:19][CH2:20][CH2:21][O:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[S:23]([C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1)([O-:25])(=[O:24])=[O:22]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 612002-Hydroxy-4-methylbenzaldehydeHCID 135229883-Methoxypropyl 4-methylbenzenesulfonate

Product 2

HCID 85570p-ToluenesulfonateYield 30%HCID 860534322-(3-Methoxypropoxy)-4-methylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-hydroxy-4-methylbenzaldehyde (3 g, 21.6 mmol), potassium carbonate (14.9 g, 107.8 mmol) and the title A compound, toluene-4-sulfonic acid 3-methoxy-propyl ester (8.07 g, 32.4 mmol) in DMF (50 mL) is stirred at 50° C. for 3 h. The solvent is concentrated under reduced pressure, H2O is added, and the aqueous layer extracted twice with ethyl acetate. The combined organic extracts are dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the title compound together with 30% of remaining tosylate: Rt (HPLC, Nucleosil C18, 10:90-100:0 CH3CN/H2O+0.1% TFA within 5 min, then 100% CH3CN+0.1% TFA): 5.25, 5.39 min. The mixture is further used as is in the next step.

Workup

  1. concentrationThe solvent is concentrated under reduced pressure, H2O
  2. additionis added
  3. extractionthe aqueous layer extracted twice with ethyl acetate
  4. dry with materialThe combined organic extracts are dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ee69d52e28544d3fb4b5648055625a5c
Source dataset
uspto-grants-2013_01
Patent number
US08362040B2

Reaction notes

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