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

HRID 75239

Reaction equation

HRID 75239 reaction equation
C([Li])CCC.[Cl:6][C:7]1[CH:8]=[C:9]([CH:21]=[C:22]([Cl:24])[CH:23]=1)[O:10][Si](C(C)C)(C(C)C)C(C)C.CN([CH:28]=[O:29])C.Cl>CCCCCC.C1COCC1>[Cl:24][C:22]1[CH:21]=[C:9]([OH:10])[CH:8]=[C:7]([Cl:6])[C:23]=1[CH:28]=[O:29]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 21594466(3,5-Dichlorophenoxy)tris(propan-2-YL)silaneHCID 178418339Butyllithium

Product 1

HCID 5283822,6-Dichloro-4-hydroxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 2.50 M n-butyllithium in hexane (13.3 mL) was added to a stirred solution of (3,5-dichlorophenoxy)(triisopropyl)silane (10.1 g, 31.6 mmol) in THF (40 mL) under an atmosphere of nitrogen at −78° C. After stirring for 45 min at −78° C., DMF (5 mL) was added slowly. The mixture was allowed to warm to −10° C. After hydrolysis with 2 N HCl, the layers were separated and the aqueous layer separated and extracted with ethyl acetate twice. The combined organic solutions were dried over Na2SO4, filtered and concentrated. To the residue was added hexane (30 mL) and the precipitate was filtered and washed with hexane to give the desired product as a white precipitate. (5.50 g, 91%). LCMS for C7H5Cl2O2(M+H)+: m/z=191.

Workup

  1. temperatureto warm to −10° C
  2. customthe layers were separated
  3. customthe aqueous layer separated
  4. extractionextracted with ethyl acetate twice
  5. dry with materialThe combined organic solutions were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. additionTo the residue was added hexane (30 mL)
  9. filtrationthe precipitate was filtered
  10. washwashed with hexane

Sources & evidence

ORD record
ord-0bd878f388884c9a990fc92cc1f14068
Source dataset
uspto-grants-2014_09
Patent number
US08835423B2

Linked notes

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