Potassium Carbonate → 2-(4-Chloro-2-formyl-phenoxy)-2-methyl-propionic acid tert-butyl ester

HRID 1728241Notes

Reaction equation

HRID 1728241 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[C:11]([O:15][C:16](=[O:21])[C:17](Br)([CH3:19])[CH3:18])([CH3:14])([CH3:13])[CH3:12].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:11]([O:15][C:16](=[O:21])[C:17]([O:10][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:9][C:6]=1[CH:7]=[O:8])([CH3:19])[CH3:18])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehydeHCID 90290tert-Butyl 2-bromo-2-methylpropionate

Product 1

HCID 575662212-(4-Chloro-2-formyl-phenoxy)-2-methyl-propionic acid tert-butyl esterYield 53.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

5-Chloro-2-hydroxy-benzaldehyde (15.6 g, 100 mmol), 2-bromo-2-methyl-propionic acid tert-butyl ester (33.4 g, 150 mmol), K2CO3 (27.6 g, 200 mmol) and KI (3 g, 19 mmol) were mixed in DMF (100 mL). Then the reaction mixture was heated at 110° C. for 3 h. The mixture was filtered and the filtrate was concentrated. The residue was dissolved in ethyl acetate and washed with 1N NaOH. Then the organic layer was separated, dried over Na2SO4 and concentrated to give title compound (16 g)

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with 1N NaOH
  5. customThen the organic layer was separated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d0ff954518c640ad8406b5d51fc488e2
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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