Chloride → HCID 131723177, compound

HRID 841121Notes

Reaction equation

HRID 841121 reaction equation
[C:1]([C:4]1[C:5]([C:23](=[O:25])[CH3:24])=[C:6]([OH:22])[C:7](=[CH:20][CH:21]=1)[C:8]([O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][OH:19])=[O:9])(=[O:3])[CH3:2].[Cl-].[C:27](OC1C(=CC=CC=1)C(O)=O)(=[O:29])[CH3:28].C(O)COCCOCCOCCO>C(N(CC)CC)C>[C:1]([C:4]1[C:5]([C:23](=[O:25])[CH3:24])=[C:6]([OH:22])[C:7](=[CH:20][CH:21]=1)[C:8]([O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:28][CH2:27][OH:29])=[O:9])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 312ChlorideHCID 2244AspirinHCID 8200Tetraethylene GlycolHCID 131723178HCID 131723178, compound

Product 1

HCID 131723177HCID 131723177, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The compound (II) was prepared according to the procedure described for the synthesis of triethylenglycol bis-acetylsalicylate (XIX), starting from 2 g of the chloride of acetylsalicylic acid, 0.93 g of tetraethylenglycol and 1.5 ml of trietylamine. The product was purified on silica gel chromatography utilizing an eluent mix constituted by methylene chloride/ethyl acetate 1:1 (v/v). The intermediate fractions were collected, the solvent was evaporated under reduced pressure and 0.6 g of tetraethylenglycol bis-acetylsalicylate (II) were obtained.

Workup

  1. customThe compound (II) was prepared
  2. customThe product was purified on silica gel chromatography
  3. additionmix
  4. customThe intermediate fractions were collected
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5cc7e0ccde574ce1b4b8b7d5b05f36d5
Source dataset
uspto-grants-2002_04
Patent number
US06369260B1

Reaction notes

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