2-Mercaptoethanol → 2-[[(4-Nitrophenyl)methyl]thio]ethanol

HRID 1864073Notes

Reaction equation

HRID 1864073 reaction equation
[SH:1][CH2:2][CH2:3][OH:4].[N+:5]([C:8]1[CH:15]=[CH:14][C:11]([CH2:12]Br)=[CH:10][CH:9]=1)([O-:7])=[O:6].C([O-])([O-])=O.[K+].[K+]>CC(C)=O.C1OCCOCCOCCOCCOCCOC1>[N+:5]([C:8]1[CH:15]=[CH:14][C:11]([CH2:12][S:1][CH2:2][CH2:3][OH:4])=[CH:10][CH:9]=1)([O-:7])=[O:6]

Participants

6

Reactant 3

HCID 15672-MercaptoethanolHCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromide

Product 1

HCID 135682062-[[(4-Nitrophenyl)methyl]thio]ethanolYield 119.3%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 180AcetoneSolvent

Procedure

β-Mercaptoethanol (3.3 mL, 47.2 mmol) was added to a suspension of 4-nitrobenzyl bromide (10.0 g, 46.3 mmol), K2CO3 (16.1 g, 116.5 mmol), KI (154 mg, 0.9 mmol), and 18-crown-6 (258 mg, 1.0 mmol) in acetone (105 mL). The mixture was refluxed under N2 for 1.5 h, cooled to room temperature, filtered through a pad of celite, and concentrated in vacuo. The filtrate was poured into water (100 mL) and extracted with Et2O (2×100 mL). The extracts were washed with brine (150 mL), dried over Na2SO4, filtered, and concentrated in vacuo to give an orange oil (11.78 g), which was used in the following step without purification. MS: M(C9H11NO3S)=213.26, (M−OH)+=196.0.

Workup

  1. temperatureThe mixture was refluxed under N2 for 1.5 h
  2. filtrationfiltered through a pad of celite
  3. concentrationconcentrated in vacuo
  4. additionThe filtrate was poured into water (100 mL)
  5. extractionextracted with Et2O (2×100 mL)
  6. washThe extracts were washed with brine (150 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5d6c5718c8c146458cbd5caa537216dc
Source dataset
uspto-grants-2009_12
Patent number
US07625903B2

Reaction notes

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