Water → (4-Formyl-3,5-dimethylphenoxy)-acetic acid methyl ester

HRID 1515001Notes

Reaction equation

HRID 1515001 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([CH3:10])[C:5]([CH:6]=[O:7])=[C:4]([CH3:11])[CH:3]=1.[CH3:12][O:13][C:14](=[O:17])[CH2:15]Br.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.CCOC(C)=O>[CH3:12][O:13][C:14](=[O:17])[CH2:15][O:1][C:2]1[CH:3]=[C:4]([CH3:11])[C:5]([CH:6]=[O:7])=[C:8]([CH3:10])[CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 5910722,6-Dimethyl-4-hydroxybenzaldehyde

Product 1

HCID 86651272(4-Formyl-3,5-dimethylphenoxy)-acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-hydroxy-2,6-dimethylbenzaldehyde (1.3 g, 8.6 mmol) and bromoacetic acid methyl ester (0.98 ml, 10.3 mmol) in DMF (20 mL) was added K2CO3 (1.8 g, 12.9 mmol). The suspension was stirred at ambient temperature overnight then the reaction mixture was partioned between water and EtOAc. The aqueous layer was extracted with EtOAc and the organic layer was dried with MgSO4, filtered and concentrated. Purification by flash chromatography using heptane/EtOAc (5:1) as eluent gave (4-formyl-3,5-dimethylphenoxy)-acetic acid methyl ester as a yellow solid.

Workup

  1. extractionThe aqueous layer was extracted with EtOAc
  2. dry with materialthe organic layer was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash chromatography

Sources & evidence

ORD record
ord-5fe6febaa28e4851821cb0caed5bb944
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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