Water → (4-Phenylsulfanylmethyl-phenyl)-methanol

HRID 1691344Notes

Reaction equation

HRID 1691344 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([S:13][CH2:14][C:15]2[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][CH:16]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O>O1CCCC1>[C:7]1([S:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([CH2:19][OH:20])=[CH:22][CH:23]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8758244-[(Phenylsulfanyl)methyl]benzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 59255239(4-Phenylsulfanylmethyl-phenyl)-methanolYield 42.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (1.95 g, 51.3 mmol) in tetrahydrofuran (50 mL) was added dropwise a tetrahydrofuran solution of 4-phenylsulfanylmethyl-benzoic acid (5 g, 20.5 mmol) described in Manufacturing Example 206-1-1, which was stirred for 30 minutes at room temperature. This mixture was cooled with ice water, and water was carefully added. The mixture was filtered through a Celite bed, and the filtrate was combined. The organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (2.01 g). The title compound was used in the following reaction without any further purification.

Workup

  1. additionwas carefully added
  2. filtrationThe mixture was filtered through a Celite bed
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-a3d9974aedcb4b59af467e20b7fa59be
Source dataset
uspto-grants-2012_04
Patent number
US08153662B2

Reaction notes

Loading…