Benzyl Alcohol → HCID 15712559, compound

HRID 2106792Notes

Reaction equation

HRID 2106792 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:11][O:12][C:13]1[CH:14]=[CH:15][C:16]2[C:20](Cl)=[C:19]([C:22](Cl)=[O:23])[S:18][C:17]=2[CH:25]=1.[O:26]1CCCC1>CO.[OH-].[Na+]>[CH3:11][O:12][C:13]1[CH:14]=[CH:15][C:16]2[C:20]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:19]([C:22]([OH:26])=[O:23])[S:18][C:17]=2[CH:25]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 125946383-Chloro-6-methoxy-1-benzothiophene-2-carbonyl chloride

Product 1

HCID 15712559HCID 15712559, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Benzyl alcohol (6.0 mls, 58 mmoles) is added dropwise to a stirred suspension of sodium hydride (2.3 g of a 60% dispersion in mineral oil, 58 mmoles) in tetrahydrofuran (15 mls) under argon. After 20 minutes a solution of 6-methoxy-3-chloro-benzo[b]-thiophene-2-carbonyl chloride (5.0 g, 19 mmoles) in warm tetrahydrofuran (60 mls) is added during 5 minutes, and the mixture is heated under reflux. After 16 hours the mixture is cooled, and stripped of solvent under reduced pressure. The residue is partitioned between water (300 mls) and ether (150 mls). The layers are separated and the aqueous phase extracted twice with ether (100 mls). The combined ether extracts are washed with saturated brine and dried over MgSO4, then stripped of solvent under reduced pressure to leave the crude ester as a syrup which also contains mineral oil. The syrup is stirred in a mixture of methanol (10 mls) and 1N sodium hydroxide (38 mls) and heated under reflux. After four hours heating is discontinued and the methanol is removed under reduced pressure. The residue is diluted with water (300 mls) and extracted twice with ether (100 mls). The aqueous solution is stirred and acidified with concentrated HCl, and the precipitate is filtered off, rinsed with water, and dried. Recrystallization from ethanol gave the pure product (2.1 g): mp=194° C. (dec).

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux
  3. temperatureAfter 16 hours the mixture is cooled
  4. customThe residue is partitioned between water (300 mls) and ether (150 mls)
  5. customThe layers are separated
  6. extractionthe aqueous phase extracted twice with ether (100 mls)
  7. washThe combined ether extracts are washed with saturated brine
  8. dry with materialdried over MgSO4
  9. customto leave the crude ester as a syrup which also contains mineral oil
  10. temperatureheated
  11. temperatureunder reflux
  12. temperatureAfter four hours heating
  13. customthe methanol is removed under reduced pressure
  14. additionThe residue is diluted with water (300 mls)
  15. extractionextracted twice with ether (100 mls)
  16. filtrationthe precipitate is filtered off
  17. washrinsed with water
  18. customdried
  19. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-7fba4d8fe63c4bb9a56a85af66d27cd3
Source dataset
uspto-grants-1990_06
Patent number
US04931459

Reaction notes

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