Water → HCID 19972408, compound

HRID 2400168Notes

Reaction equation

HRID 2400168 reaction equation
[Na].[Cl:2][CH2:3][C:4]1[C:13]2[O:12][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:10]([CH3:20])[C:9](=[O:21])[C:8]=2[CH:7]=[CH:6][CH:5]=1.O.[O:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>C1(C)C(C)=CC=CC=1.C(O)CO>[Cl:2][CH2:3][C:4]1[C:13]2[O:12][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:10]([CH3:20])[C:9](=[O:21])[C:8]=2[CH:7]=[CH:6][CH:5]=1.[OH:23][CH2:28][CH2:27][O:26][CH2:25][C:24]1[C:13]2[O:12][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:10]([CH3:20])[C:9](=[O:21])[C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 962WaterHCID 312751,4-DioxaneHCID 5360545SodiumHCID 19972408HCID 19972408, compound

Product 2

HCID 19972408HCID 19972408, compoundHCID 19972532HCID 19972532, compound

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 7237O-XyleneSolvent

Procedure

A solution of 2.5 g of Intermediate X in 25 ml of xylene and 3 ml of dioxane was prepared. 0.15 g of sodium was dissolved in 3.10 ml of anhydrous ethylene glycol, and this solution was added dropwise at ambient temperature to the solution of Intermediate X, and then refluxed for 5.5 hours. The reaction mixture was cooled to ambient temperature, poured into 50 ml of water and extracted with dichloromethane. The extract was washed with a sodium chloride solution, dried on anhydrous sodium sulphate and evaporated to dryness in vacuo. The solid residue was crystallized from ethanol, to give 2.1 g of the title compound, melting point 132°-133° C.

Workup

  1. temperaturerefluxed for 5.5 hours
  2. extractionextracted with dichloromethane
  3. washThe extract was washed with a sodium chloride solution
  4. dry with materialdried on anhydrous sodium sulphate
  5. customevaporated to dryness in vacuo
  6. customThe solid residue was crystallized from ethanol

Sources & evidence

ORD record
ord-4e01e734bf3b4f0b9bd75466d8ecd035
Source dataset
uspto-grants-1995_09
Patent number
US05453518

Reaction notes

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