Chloroform → HCID 86601165, compound

HRID 1173315Notes

Reaction equation

HRID 1173315 reaction equation
[CH:1]([Cl:4])([Cl:3])[Cl:2].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:15]=[O:16])[CH:10]=[C:11]([CH:13]=[O:14])[CH:12]=1.[OH-].[K+]>CN(C=O)C.CO>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:15]([OH:16])[C:1]([Cl:4])([Cl:3])[Cl:2])[CH:10]=[C:11]([CH:13]([OH:14])[C:1]([Cl:4])([Cl:3])[Cl:2])[CH:12]=1

Participants

6

Reactant 3

HCID 6212ChloroformHCID 14797Potassium HydroxideHCID 108882575-methoxyisophthalaldehyde

Product 1

HCID 86601165HCID 86601165, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 0.60 g (5 mmol) of chloroform in 2 mL DMF was added 0.1 64 g (1.0 mmol) of 5-methoxy-1,3-diformylbenzene (Provent, C; Chautemps, P.; Gellon, G.; Pierre, J.-L. Tetrahedron Lett. 1996, 347 1393-96). The reaction mixture was chilled to 0° C. and a solution of 39.5 mg (0.7 mmol) of potassium hydroxide in 0.2 mL of methanol was added. The reaction mixture was stirred for 20 min at 0° C., then was quenched by addition of 1 mL of 1 N hydrochloric acid. The reaction mixture was adjusted to pH=7, then extracted with EtOAc. The organic layers were washed with brine, dried (Na2SO4), filtered and evaporated. The product was used in the next step without further purification.

Workup

  1. customwas quenched by addition of 1 mL of 1 N hydrochloric acid
  2. extractionextracted with EtOAc
  3. washThe organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe product was used in the next step without further purification

Sources & evidence

ORD record
ord-3d0326c92a2648aca394ab160b3b2d1d
Source dataset
uspto-grants-2010_11
Patent number
US07834062B2

Reaction notes

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