4-Nitrophenethyl alcohol → HCID 12942079, compound

HRID 716734Notes

Reaction equation

HRID 716734 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][OH:17])=[CH:11][CH:10]=1)([O-:8])=[O:7].CCN(CC)CC.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[CH3:1][S:2]([O:17][CH2:16][CH2:15][C:12]1[CH:11]=[CH:10][C:9]([N+:6]([O-:8])=[O:7])=[CH:14][CH:13]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 74944-Nitrophenethyl alcoholHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 12942079HCID 12942079, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Under a nitrogen atmosphere, MsCl (13.9 mL) was dropwise added to a suspension of 2-(4-nitrophenyl)ethanol (25.0 g) and Et3N (31.3 mL) in CHCl3 (including amylene, 625 mL) over 10 minutes under ice cooling, followed by stirring at room temperature for 2 hours. A saturated aqueous NaHCO3 solution was added to the reaction solution, and the aqueous layer was extracted with CHCl3. The combined organic layer was dried over MgSO4, and then the desiccant was removed by filtration. The filtrate was concentrated under reduced pressure to yield the title compound (41.8 g, light yellow solid).

Workup

  1. extractionthe aqueous layer was extracted with CHCl3
  2. dry with materialThe combined organic layer was dried over MgSO4
  3. customthe desiccant was removed by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8626f443ae0b43f398e8de63cce2148a
Source dataset
uspto-grants-2015_11
Patent number
US09193695B2

Reaction notes

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