Hydrochloric Acid → HCID 23448419, compound

HRID 1838781Notes

Reaction equation

HRID 1838781 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].[Cl:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18].N1C=CC=CC=1.Cl>>[Cl:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:6]([C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)=[O:7]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 682422-Furancarbonyl chlorideHCID 900121-Octanol, 8-chloro-

Product 1

HCID 23448419HCID 23448419, compoundYield 94%

Procedure

A solution of 2-furoyl chloride (6.5 g; 50 mmol) was added dropwise at 0° C. to a solution of 8-chloro-1-octanol (6.6 g; 40 mmol) and pyridine (20 g; 253 mmol) and stirred at room temperature for 2 h. The resulting mixture was added to a mixture of 1N-hydrochloric acid and ice (200 ml) and extracted with ethyl acetate (3×80 ml). The combined organic layers were washed with saturated sodium chloride solution (2×80 ml), dried over magnesium sulphate and filtered. The organic solvent was removed in vacuo to give 8-chlorooctyl-2-furancarboxylate (9.7 g) (94%) as an oil.

Workup

  1. extractionextracted with ethyl acetate (3×80 ml)
  2. washThe combined organic layers were washed with saturated sodium chloride solution (2×80 ml)
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customThe organic solvent was removed in vacuo

Sources & evidence

ORD record
ord-69d5b1bb083b495dad81aa7c2a1ec5b3
Source dataset
uspto-grants-2004_01
Patent number
US06676851B1

Reaction notes

Loading…