Hydrochloric Acid → HCID 178524980, compound

HRID 1609709Notes

Reaction equation

HRID 1609709 reaction equation
[CH2:1]1[C@:6]2([OH:10])[C:7]([O:9][C@@H:4]([CH2:5]2)[C@@H:3]([OH:11])[C@H:2]1[OH:12])=[O:8].Cl.C(=O)(O)[O-:15].[Na+].[Na+].[Cl-]>C1COCC1>[CH2:5]1[C@@H:4]([OH:9])[C@@H:3]([OH:11])[C@H:2]([OH:12])[CH2:1][C@@:6]1([C:7]([OH:15])=[O:8])[OH:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 101711082HCID 101711082, compound

Product 1

HCID 178524980HCID 178524980, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 12.7 g (12.2 mmol) 1,3-O-dicarbotrichloroethoxy-4-O-dicarbotrichloroethoxycaffeoyl quinide in 870 ml THF is treated for 3 days with 9 ml concentrated HCl. After cooling to 0° C., the reaction mixture is adjusted to pH 2 by addition of solid sodium bicarbonate and is then saturated with NaCl. The organic phase is then separated and the aqueous phase is extracted with 2×20 ml ethyl acetate. After the combined organic phases have been dried over sodium sulfate, the solvents are evaporated. Treatment of the residue with a solvent mixture of THF and hexane in a ratio by volume of 1:20 gives 12.7 g 1,3-O-dicarbotrichloroethoxy- 4-O-dicarbotrichloroethoxycaffeoyl quinic acid in the form of an amorphous white powder (yield 99%) .

Workup

  1. customThe organic phase is then separated
  2. extractionthe aqueous phase is extracted with 2×20 ml ethyl acetate
  3. dry with materialAfter the combined organic phases have been dried over sodium sulfate
  4. customthe solvents are evaporated
  5. additionTreatment of the residue with a solvent mixture of THF and hexane in a ratio by volume of 1:20

Sources & evidence

ORD record
ord-ec502971b7a149b8aaa5dd29058f5f42
Source dataset
uspto-grants-1995_03
Patent number
US05401858

Reaction notes

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