Sodium → 2-(4-Hydroxy-5-methoxy-2-methyl-phenoxy)-2-methyl-propionic acid methyl ester

HRID 852429Notes

Reaction equation

HRID 852429 reaction equation
[Na].[CH2:2]([O:4][C:5](=[O:23])[C:6]([O:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18]C(=O)C)=[CH:12][C:11]=1[CH3:22])([CH3:8])[CH3:7])C>CO>[CH3:2][O:4][C:5](=[O:23])[C:6]([O:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]([OH:18])=[CH:12][C:11]=1[CH3:22])([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 5360545SodiumHCID 674024992-(4-Acetoxy-5-methoxy-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester

Product 1

HCID 674032312-(4-Hydroxy-5-methoxy-2-methyl-phenoxy)-2-methyl-propionic acid methyl esterYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A freshly prepared solution of 91 mg (4 mmol) sodium in 5.4 ml methanol was added within 5 min to an ice cooled solution of 235 mg (0.8 mmol) 2-(4-acetoxy-5-methoxy-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester in 5.4 ml methanol. The solution was naturally warmed to ambient temperature and after 5 h the solvent was removed under reduced pressure. Ice water/1 M HCl 1/1 was added and the mixture was extracted two times with dichloromethane. The combined extracts were dried over sodium sulfate and the solvent was removed under reduced pressure to yield 153 mg (0.6 mmol, 76%) of the title compound as brown oil which was used in the next step without further purification.

Workup

  1. customwas removed under reduced pressure
  2. additionIce water/1 M HCl 1/1 was added
  3. extractionthe mixture was extracted two times with dichloromethane
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e5d21fe6fc154c638f37accc94c06c83
Source dataset
uspto-grants-2007_08
Patent number
US07253192B2

Reaction notes

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