Hydrochloric Acid → [2-(Benzylsulfanyl)phenyl]methanol

HRID 11310

Reaction equation

HRID 11310 reaction equation
[CH2:1]([S:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11](O)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].CO.Cl>O1CCCC1>[CH2:1]([S:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[CH2:11][OH:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 2641822-(Benzylsulfanyl)benzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 10977293[2-(Benzylsulfanyl)phenyl]methanolYield 63.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-benzylsulfanyl benzoic acid 3 (50 mg, 0.206 mmol) in THF at 0° C. was added LiAlH4 (0.62 mL of a 1.0 mL solution in THF, 0.62 mmol) and the mixture was stirred at 0° C. for 15 minutes then allowed to warm to room temperature. The solution was stirred for 2 hours. The mixture was cooled at 0° C. then methanol (MeOH) was added slowly followed by HCl (0.5N) and tetrahydrofuran (THF). The mixture was stirred at room temperature for 30 minutes. It was then concentrated to remove THF, extracted with CH2Cl2 (3X), dried over MgSO4, filtered and concentrated to give 30 mg of the product as a yellow oil.

Workup

  1. temperatureto warm to room temperature
  2. stirringThe solution was stirred for 2 hours
  3. temperatureThe mixture was cooled at 0° C.
  4. stirringThe mixture was stirred at room temperature for 30 minutes
  5. concentrationIt was then concentrated
  6. customto remove THF
  7. extractionextracted with CH2Cl2 (3X)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-63615ad3fdcf46798ec103c948af08a5
Source dataset
uspto-grants-2006_08
Patent number
US07098223B2

Linked notes

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