HCID 18992101, compound → HCID 18992046, compound

HRID 375713Notes

Reaction equation

HRID 375713 reaction equation
C[O:2][C:3]1[C:4]([CH3:20])=[C:5]([C:14]([CH3:19])=[C:15]([O:17]C)[CH:16]=1)[C:6]([O:8][CH2:9][C:10]([Cl:13])([Cl:12])[Cl:11])=[O:7]>C(Cl)Cl>[OH:2][C:3]1[C:4]([CH3:20])=[C:5]([C:14]([CH3:19])=[C:15]([OH:17])[CH:16]=1)[C:6]([O:8][CH2:9][C:10]([Cl:11])([Cl:12])[Cl:13])=[O:7]

Participants

3

Reactant 1

HCID 18992101HCID 18992101, compound

Product 1

HCID 18992046HCID 18992046, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2.73 g of 2,2,2-trichloroethyl 3,5-dimethoxy-2,6-dimethylbenzoate in 8 ml of methylene chloride was cooled to -78° C., whereupon the dissolved material partly precipitated. To the stirred mixture a solution of 6.01 g of boron tribromide in 8 ml of methylene chloride was added dropwise within 20 minutes. During the addition a clear solution formed, but later on a precipitate formed again. After stirring for 10 minutes at -78° C. and for 2.5 hours at 0° C., the reaction mixture was poured on ice water with stirring, and the aqueous layer was extracted with methylene chloride. The organic layer was washed with water, dried over sodium sulphate and evaporated to dryness in vacuo. The residue was chromatographed on silica gel using acetone/n-hexane (1:3, v/v) for the elution. Crystallization of the purified product from ethyl acetate/n-hexane afforded 2,2,2-trichloroethyl 3,5-dihydroxy-2,6-dimethylbenzoate as white crystals with mp 132°-133° C.

Workup

  1. custompartly precipitated
  2. additionTo the stirred mixture a solution of 6.01 g of boron tribromide in 8 ml of methylene chloride was added dropwise within 20 minutes
  3. additionDuring the addition a clear solution
  4. customformed
  5. customlater on a precipitate formed again
  6. additionthe reaction mixture was poured on ice water
  7. stirringwith stirring
  8. extractionthe aqueous layer was extracted with methylene chloride
  9. washThe organic layer was washed with water
  10. dry with materialdried over sodium sulphate
  11. customevaporated to dryness in vacuo
  12. customThe residue was chromatographed on silica gel
  13. washv/v) for the elution
  14. customCrystallization of the purified product from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-216c13902b174879bc8f42913ad52a47
Source dataset
uspto-grants-1996_01
Patent number
US05486466

Reaction notes

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