Nitrate → (2,2-Dimethyl-1,3-dioxolan4-yl)methyl 4-nitrobenzenesulfonate

HRID 1490050Notes

Reaction equation

HRID 1490050 reaction equation
N1C=CC=CC=1.[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1)([O-:9])=[O:8].[CH3:20][C:21]1([CH3:28])[O:25][CH:24]([CH2:26][OH:27])[CH2:23][O:22]1.[N+]([O-])([O-])=O>ClCCl>[N+:7]([C:10]1[CH:11]=[CH:12][C:13]([S:16]([O:27][CH2:26][CH:24]2[CH2:23][O:22][C:21]([CH3:28])([CH3:20])[O:25]2)(=[O:18])=[O:17])=[CH:14][CH:15]=1)([O-:9])=[O:8]

Participants

6

Reactant 4

HCID 943NitrateHCID 1049PyridineHCID 74044-Nitrobenzenesulfonyl chlorideHCID 7528Solketal

Product 1

HCID 21596214(2,2-Dimethyl-1,3-dioxolan4-yl)methyl 4-nitrobenzenesulfonateYield 72.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (29.96 g, 0.37 mol) was added to a solution of 4-nitrobenzenesulfonyl chloride (58.7 g, 0.26 mol) in dichloromethane (300 mL) at 0° C. followed by the dropwise addition of 2,2-dimethyl-1,3-dioxolane-4-methanol (50 g, 0.37 mol). After stirring the mixture at temperature for 1 h, the reaction mixture was allowed to warm to room temperature and stirring continued for 4 h. The reaction nitrate was washed with 1N HCl (2×200 mL), dried (MgSO4), and evaporated to a solid which was recrystallized (ethyl acetate/hexane) to give 60 g (50%) of the desired product: mp 92°-94° C.

Workup

  1. stirringstirring
  2. waitcontinued for 4 h
  3. washwas washed with 1N HCl (2×200 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated to a solid which
  6. customwas recrystallized (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c2752079dcbd4e51bb6163cb0b397554
Source dataset
uspto-grants-1997_10
Patent number
US05681834

Reaction notes

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