Acetic Acid → 2,6-Dichloro-3-methoxybenzaldehyde

HRID 2235208Notes

Reaction equation

HRID 2235208 reaction equation
C([Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[Cl:16])(C)C)(C)(C)C.C([Li])(CC)C.CN(C)[CH:24]=[O:25].[C:27](O)(=O)C>O1CCCC1.O>[Cl:16][C:10]1[C:9]([O:8][CH3:27])=[CH:14][CH:13]=[C:12]([Cl:15])[C:11]=1[CH:24]=[O:25]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 59803885Tert-butyl(2,4-dichlorophenoxy)dimethylsilaneHCID 178418400CID 53628100

Product 1

HCID 149271732,6-Dichloro-3-methoxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Dissolve tert-Butyl-(2,4-dichloro-phenoxy)-dimethyl-silane (48.4 g, 175 mmol) in tetrahydrofuran (575ml) and cool to −78° C. Add sec-butyl lithium (1.4M, 131 ml, 183 mmol) slowly at −78° C. and stir at −78° C. for 30 minutes. Add N,N-dimethylformamide and stir at −78° C. for 1.5 hours. Pour reaction mixture into acetic acid in water (1:12, 830 ml) and stir warming to room temperature. Extract with ether, wash with water, brine dry over sodium sulfate, filter and concentrate to yield a mixture of the title compound and TBS protected analog. Slur in hexanes and filter to yield 15 g (45%) of 2,6-dichloro-3-hydroxy-benzaldehyde.

Workup

  1. additionPour
  2. temperaturewarming to room temperature
  3. extractionExtract with ether
  4. washwash with water, brine
  5. dry with materialdry over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate
  8. customto yield

Sources & evidence

ORD record
ord-f7337673e5b34fe082ebc72da7c1c763
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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