Hydrochloric Acid → 2,6-Dichloro-4-hydroxybenzaldehyde

HRID 1514993Notes

Reaction equation

HRID 1514993 reaction equation
C([Si]([O:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([Cl:16])[CH:10]=1)(C)C)(C)(C)C.[Li]C(CC)C.CN([CH:25]=[O:26])C.Cl>C1COCC1.C1CCCCC1>[Cl:16][C:11]1[CH:10]=[C:9]([OH:8])[CH:14]=[C:13]([Cl:15])[C:12]=1[CH:25]=[O:26]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 18007485Tert-butyl(3,5-dichlorophenoxy)dimethylsilaneHCID 178418400CID 53628100

Product 1

HCID 5283822,6-Dichloro-4-hydroxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8078CyclohexaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of tert-butyl-(3,5-dichlorophenoxy)-dimethylsilane (2.7 g, 9.8 mmol) in THF (20 mL) at −78° C., under a N2 atmosphere, was added dropwise sec-BuLi (7.2 mL of a 1.4 M solution in cyclohexane, 10.1 mmol). After 30 min, anhydrous DMF (1.2 mL, 15.2 mmol) was added slowly to the solution. After the addition, the solution was stirred at −78° C. for 1.5 h then 20 mL of 1N HCl was added and the suspension was warmed to ambient temperature. The aqueous layer was extracted with EtOAc and the organic layer was washed with water, brine, dried with MgSO4 and filtered. The solvent was removed under reduced pressure to give 2,6-dichloro-4-hydroxybenzaldehyde as a pale yellow solid.

Workup

  1. additionAfter the addition
  2. temperaturethe suspension was warmed to ambient temperature
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washthe organic layer was washed with water, brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-866f4996f30249489047376111e6f053
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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