Hydrochloric Acid → HCID 69881217, compound

HRID 1108134Notes

Reaction equation

HRID 1108134 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[CH2:11][CH2:12][C:13](=[O:31])[CH2:14][CH2:15][S:16][CH2:17][CH2:18][C:19](=[O:30])[CH2:20][CH2:21][C:22]1[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][C:23]=1[CH3:29].Cl>C(O)C>[CH3:29][C:23]1[CH:24]=[CH:25][C:26]([CH3:28])=[CH:27][C:22]=1[CH2:21][CH2:20][CH:19]([OH:30])[CH2:18][CH2:17][S:16][CH2:15][CH2:14][CH:13]([OH:31])[CH2:12][CH2:11][C:5]1[CH:6]=[C:7]([CH3:10])[CH:8]=[CH:9][C:4]=1[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 69879303HCID 69879303, compound

Product 1

HCID 69881217HCID 69881217, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.65 g (43.6 mmol) of sodium borohydride was gradually added to 16.1 g (72.6 mmol) of the (2,5-dimethylphenyl)-3-oxopentylsulfide and 64 ml of ethanol at 0° C., and the mixture was stirred at room temperature for 1 hour. The mixture was poured into ice and an aqueous solution containing 5% hydrochloric acid and extracted with dichloroethane. The extract was dried over anhydrous sodium sulfate and filtered, and the solvent was distilled off under reduced pressure to give 16.3 g of (2,5-dimethylphenyl)-3-hydroxypentylsulfide in the form of a colorless transparent oil.

Workup

  1. additionThe mixture was poured into ice
  2. extractionextracted with dichloroethane
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-ed74f263810c4b9da53645f2b03c254c
Source dataset
uspto-grants-2000_05
Patent number
US06063936

Reaction notes

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