Acetonitrile → Ethyl (4-formyl-2-methylphenoxy)acetate

HRID 1269589Notes

Reaction equation

HRID 1269589 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:10].C(#N)C.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:3]([CH3:10])[CH:4]=1)=[O:7]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 1399014-Hydroxy-3-methylbenzaldehyde

Product 1

HCID 58622891Ethyl (4-formyl-2-methylphenoxy)acetateYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-hydroxy-3-methylbenzaldehyde (8 g, 58.8 mmol) in an hydrous acetonitrile (300 mL), under nitrogen at 0° C., was added caesium carbonate (21 g, 64.6 mmol) and ethyl bromoacetate (6.52 mL, 58.8 mmol). The resulting mixture was allowed to come to room temperature and stirred for 16 h. The reaction mixture was diluted with water (400 mL) and extracted with EtOAc (2×500 mL). The combined organic extracts were dried (MgSO4) and the solvents removed in vacuo, to afford the title compound as brown solid (11.5 g).

Workup

  1. customto come to room temperature
  2. extractionextracted with EtOAc (2×500 mL)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-473f17f55b5d4d3d9b9c45fd62fa22b3
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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