Chloride → HCID 131723177, compound

HRID 841122Notes

Reaction equation

HRID 841122 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)CCCCCO>>[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

5

Reactant 4

HCID 312ChlorideHCID 2244AspirinHCID 123741,6-HexanediolHCID 131723178HCID 131723178, compound

Product 1

HCID 131723177HCID 131723177, compound

Procedure

The compound was prepared according to the procedure described in Example 1 for the synthesis of (XIX), prepared starting from 6 g of the chloride of acetylsalicylic acid, 4.6 ml of TEA and 1.9 g of 1.6-hexandiol. The product was purified by flash chromatography utilizing an eluent mix constituted by ethylether/hexane 7:3 (v/v). The intermediate fractions were collected, the solvent was evaporated under reduced pressure and a solid residue was obtained which, triturated with isopropyl ether, produced 1 g of 1.6-hexandiol bis-acetylsalicylate (II) with m.p.=96° C.

Workup

  1. customThe compound was prepared
  2. customprepared
  3. customThe product was purified by flash chromatography
  4. additionmix
  5. customThe intermediate fractions were collected
  6. customthe solvent was evaporated under reduced pressure
  7. customa solid residue was obtained which
  8. customtriturated with isopropyl ether

Sources & evidence

ORD record
ord-98a7cae27e9d47be888dcb8189137ed1
Source dataset
uspto-grants-2002_04
Patent number
US06369260B1

Reaction notes

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