Water → 3-(2-Mercaptobenzyl)phenol

HRID 1987482Notes

Reaction equation

HRID 1987482 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[SH:13].[Al+3].[Cl-].[Cl-].[Cl-].[Li]CCCC.O>CCCCCC.C(OCC)(=O)C>[SH:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH2:6][C:5]1[CH:4]=[C:3]([OH:2])[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 686436202-(3-Methoxybenzyl)benzenethiolHCID 178418339Butyllithium

Product 1

HCID 686436703-(2-Mercaptobenzyl)phenolYield 40%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a mixture of 0.61 g 2-(3-methoxybenzyl)benzenethiol (L) (2.65 mmol) and 1.94 g AlCl3 was added slowly 1.2 eq n-BuLi. The reaction was stirred overnight before 30 ml water was added. The mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine and dried over magnesium sulfate. The volatiles were removed by distillation under nitrogen. Flash silica chromatography (hexane:ethyl acetate 80:20) afforded 0.23 g product (1.06 mmol, 40% yield).

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe volatiles were removed by distillation under nitrogen

Sources & evidence

ORD record
ord-79c4a270219a43efa25005df2eeb39a0
Source dataset
uspto-grants-2009_06
Patent number
US07550505B2

Reaction notes

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