Cesium carbonate → Ethyl 2-(4-formyl-2-methylphenoxy)-2-methylpropanoate

HRID 1269588Notes

Reaction equation

HRID 1269588 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:10].Br[C:12]([CH3:19])([CH3:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][C:12]([CH3:19])([CH3:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:3]([CH3:10])[CH:4]=1)=[O:7]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 1399014-Hydroxy-3-methylbenzaldehyde

Product 1

HCID 18448413Ethyl 2-(4-formyl-2-methylphenoxy)-2-methylpropanoateYield 63.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 4-hydroxy-3-methyl benzaldehyde (3 g, 22 mmol) and ethyl 2-bromo-2-methylpropionate (6.5 mL, 44 mmol) in DMF (100 mL) was added caesium carbonate (15.8 g, 48 mmol). The resulting mixture was heated at 40° C. for 42 h, then allowed to cool to room temperature. The reaction mixture was diluted with water (200 mL) and extracted with EtOAc (2×150 mL). The organic solution was dried (MgSO4), filtered and evaporated. Purification by Biotage™ chromatography (Silica, 90 g) eluting 9:1 cyclohexane:EtOAc afforded the title compound as a pale yellow oil (3.5 g).

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with EtOAc (2×150 mL)
  3. dry with materialThe organic solution was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by Biotage™ chromatography (Silica, 90 g)
  7. washeluting 9:1 cyclohexane

Sources & evidence

ORD record
ord-8482b67786f944fba52a1da2334fb96c
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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