Water → 4-(3-Chloropropylthio)benzylalcohol

HRID 1789366Notes

Reaction equation

HRID 1789366 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][CH2:8][CH2:9][CH2:10][S:11][C:12]1[CH:21]=[CH:20][C:15]([C:16](OC)=[O:17])=[CH:14][CH:13]=1.O>O1CCCC1>[Cl:7][CH2:8][CH2:9][CH2:10][S:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:16][OH:17])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 13749599Methyl 4-(3-chloropropylthio)benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 137496004-(3-Chloropropylthio)benzylalcoholYield 85.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5 g of lithium aluminum hydride are suspended in 200 ml of tetrahydrofuran, and a solution of 31.9 g of methyl 4-(3-chloro-propylthio)benzoate in 200 ml of tetrahydrofuran is added thereto at 5° to 15° C. The mixture is stirred at the same temperature for 45 minutes. Water is added to the mixture at a temperature of below 20° C., and insoluble materials are filtered off. The filtrate is concentrated under reduced pressure to remove solvent, and the residue is distilled under reduced pressure. 24.1 g of 4-(3-chloropropylthio)benzylalcohol are obtained as an oil. Yild: 85%.

Workup

  1. customat 5° to 15° C
  2. filtrationare filtered off
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. customto remove solvent
  5. distillationthe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-60e4dc598c6f440faebfb4ac0e619073
Source dataset
uspto-grants-1987_08
Patent number
US04689327

Reaction notes

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