Water → 4-(2-Amino-4-hydroxymethyl-phenylsulfanyl)-phenol

HRID 607223Notes

Reaction equation

HRID 607223 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[C:6]([NH2:18])[CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[NH2:18][C:6]1[CH:5]=[C:4]([CH2:3][OH:2])[CH:9]=[CH:8][C:7]=1[S:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 668086283-Amino-4-(4-hydroxy-phenylsulfanyl)-benzoic acid methyl ester

Product 1

HCID 668084044-(2-Amino-4-hydroxymethyl-phenylsulfanyl)-phenolYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To the product from Example 113B (500 mg, 1.82 mmol) in tetrahydrofuran (50 mL) was added a solution of lithium aluminum hydride (1.0M in THF, 1.8 mL, 1.82 mmol) dropwise at room temperature followed by heating the mixture to 70° C. for 4 hours. Water (25 mL) was then carefully added to the solution and the organic layer separated, dried and concentrated under vacuum to provide the title compound (295 mg, 66%).

Workup

  1. customthe organic layer separated
  2. customdried
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4e13a3b1c943457f839a5c5b3d2bfa7c
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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