Ammonia → 2-(2-Mercaptobenzyl)phenol

HRID 1987479Notes

Reaction equation

HRID 1987479 reaction equation
C[S:2][C:3]1[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=1[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12].N.[Na].[NH4+].[Cl-]>CCCCCC.C(OCC)(=O)C.C1COCC1>[SH:2][C:3]1[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=1[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 686436452-(2-(Methylthio)benzyl)phenol

Product 1

HCID 686436382-(2-Mercaptobenzyl)phenolYield 71.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 0.68 g 2-(2-(methylthio)benzyl)phenol (I) (2.96 mmol) in 4 ml freshly distilled THF at −78° C. was added 8 mL condensed ammonia followed by 0.15 g sodium. The blue solution was stirred for 2 hours at −78° C. before the mixture was warmed to ambient temperature. The reaction was allowed to stir overnight before NH4Cl was added until neutral. The mixture was extracted with ethyl acetate and the combined organic extracts washed with brine, dried over magnesium sulfate and concentrated. Flash silica chromatography (hexane:ethyl acetate 80:20) afforded 0.457 g product (2.12 mmol, 71% yield).

Workup

  1. temperaturewas warmed to ambient temperature
  2. additionwas added until neutral
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe combined organic extracts washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5f52a805e826418eab7d7b4187cbb477
Source dataset
uspto-grants-2009_06
Patent number
US07550505B2

Reaction notes

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