Hydrochloric Acid → HCID 23450683, compound

HRID 368945Notes

Reaction equation

HRID 368945 reaction equation
[CH2:1]([CH:3]1[C:12]2[C:7](=[C:8]([CH3:14])[CH:9]=[CH:10][C:11]=2[CH3:13])[S:6][CH2:5][CH2:4]1)[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[C:19](Cl)(=[O:21])[CH3:20].Cl>ClCCl>[C:19]([C:10]1[C:11]([CH3:13])=[C:12]2[C:7](=[C:8]([CH3:14])[CH:9]=1)[S:6][CH2:5][CH2:4][CH:3]2[CH2:1][CH3:2])(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 23450674HCID 23450674, compound

Product 1

HCID 23450683HCID 23450683, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixed solution containing 1.91 g (9.26 mmol) of the 4-ethyl-5,8-dimethylthiochroman and dichloromethane was dropwise added to a mixed solution containing 1.49 g (11.1 mmol) of aluminum chloride, 0.82 ml (11.6 mmol) of acetyl chloride and 6 ml of dichloromethane at 0° C., and the mixture was stirred for 1.5 hours. The reaction mixture was poured into ice and a solution containing 5% hydrochloric acid and extracted with dichloromethane. The extract was washed with a saturated sodium hydrogencarbonate, dried over anhydrous sodium sulfate and filtered, and the solvent was distilled off under reduced pressure to give 1.66 g (yield 72%) of 6-acetyl-4-ethyl-5,8-dimethylthiochroman.

Workup

  1. additionwas dropwise added to a mixed solution
  2. additionThe reaction mixture was poured into ice
  3. extractionextracted with dichloromethane
  4. washThe extract was washed with a saturated sodium hydrogencarbonate
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f902ae288cad46c497394718f4e4d60f
Source dataset
uspto-grants-2000_10
Patent number
US06136755

Reaction notes

Loading…