Triethylamine → 2-(Methanesulfonyloxymethyl)-6-methyl-nitrobenzene

HRID 1421386Notes

Reaction equation

HRID 1421386 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][C:7]1[C:8]([N+:15]([O-:17])=[O:16])=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH2:10][OH:11].C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([O:11][CH2:10][C:9]1[CH:12]=[CH:13][CH:14]=[C:7]([CH3:6])[C:8]=1[N+:15]([O-:17])=[O:16])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 5619893-Methyl-2-nitrobenzenemethanol

Product 1

HCID 157669562-(Methanesulfonyloxymethyl)-6-methyl-nitrobenzeneYield 97.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At 10-15° C., 27 g (0.23 mol) of methanesulfonyl chloride dissolved in 20 ml of CH2Cl2 is dripped into a mixture of 34 g (0.2 mol) of 3-methyl-2-nitrobenzyl alcohol and 27 g (0.27 mol) of triethylamine in 100 ml of CH2Cl2. The reaction mixture is stirred for 1 hour at room temperature and is then extracted with water. The organic phase is dried over MgSO4 and evaporated down. There is obtained as residue 48 g of the title compound as a yellow oil, containing about 10% of the corresponding benzyl chloride as impurity. The crude product is used for the next reaction without any further purification.

Workup

  1. extractionis then extracted with water
  2. dry with materialThe organic phase is dried over MgSO4
  3. customevaporated down

Sources & evidence

ORD record
ord-ba8c9db75c98483a93115c81cefa7bd9
Source dataset
uspto-grants-2000_06
Patent number
US06075148

Reaction notes

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