Ethanol → HCID 15278511, compound

HRID 374411Notes

Reaction equation

HRID 374411 reaction equation
[Br:1][C:2]1[C:3]([CH3:14])=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[S:8][CH2:7][CH2:6][CH:5]2[OH:13].[CH2:15](O)[CH3:16]>S(=O)(=O)(O)O.O>[Br:1][C:2]1[C:3]([CH3:14])=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[S:8][CH2:7][CH2:6][CH:5]2[O:13][CH2:15][CH3:16]

Participants

5

Reactant 2

HCID 702EthanolHCID 234507086-Bromo-5,8-dimethylthiochroman-4-ol

Product 1

HCID 15278511HCID 15278511, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Procedure

A 100 ml three-necked flask was charged with 5.9 g (0.022 mol) of 6-bromo-5,8-dimethylthiochroman-4-one, and then, 30 ml of methylene chloride and 10 ml of methanol were added and dissolved. The entire reaction system was cooled to 0° C. in an ice salt bath, and 0.42 g.(0.011 mol) of sodium borohydride was added by small portions. Thereafter, the mixture was allowed to react for 2 hours while it was cooled as above. The reaction mixture was poured into 100 ml of water, and the mixture was extracted with methylene chloride. The extract was dried over anhydrous sodium sulfate, and methylene chloride was distilled off under reduced pressure to give 6.0 g of 6-bromo-5,8-dimethyl-4-hydroxythiochroman as a solid. Then, 6.0 g of this 6-bromo-5,8-dimethyl-4-hydroxythiochroman was charged into a 100 ml eggplant-shaped flask, and 20 ml of ethanol was added to form a solution. Then, 10 drops of concentrated sulfuric acid was added, and the mixture was refluxed under heat for 1 hour. The reaction mixture was allowed to cool and poured into 100 ml of water, and the mixture was extracted with methylene chloride. The extract was dried over anhydrous sodium sulfate, and methylene chloride was distilled off under reduced pressure to give 5.8 g of 6-bromo-5,8-dimethyl-4-ethoxythiochroman as an oily substance.

Workup

  1. customto form a solution
  2. temperaturethe mixture was refluxed
  3. temperatureunder heat for 1 hour
  4. temperatureto cool
  5. extractionthe mixture was extracted with methylene chloride
  6. dry with materialThe extract was dried over anhydrous sodium sulfate, and methylene chloride
  7. distillationwas distilled off under reduced pressure

Sources & evidence

ORD record
ord-2eb228e01f844f3b91bc437742cef810
Source dataset
uspto-grants-1996_01
Patent number
US05480858

Reaction notes

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