2,3,4,6-Tetramethyl-benzene-sulfonic acid → 2-Oxopentyl-2,3,4,6-tetramethylbenzene sulfonate

HRID 1154349Notes

Reaction equation

HRID 1154349 reaction equation
[N+](=[CH:3][C:4](=[O:8])[CH2:5][CH2:6][CH3:7])=[N-].[CH3:9][C:10]1[C:15]([CH3:16])=[C:14]([CH3:17])[CH:13]=[C:12]([CH3:18])[C:11]=1[S:19]([OH:22])(=[O:21])=[O:20]>CCOCC>[O:8]=[C:4]([CH2:5][CH2:6][CH3:7])[CH2:3][O:22][S:19]([C:11]1[C:12]([CH3:18])=[CH:13][C:14]([CH3:17])=[C:15]([CH3:16])[C:10]=1[CH3:9])(=[O:20])=[O:21]

Participants

4

Reactant 2

HCID 133101902,3,4,6-Tetramethyl-benzene-sulfonic acidHCID 537665711-Diazopentan-2-one

Product 1

HCID 130032542-Oxopentyl-2,3,4,6-tetramethylbenzene sulfonateYield 60%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 1.0 g quantity of 1-diazo-2-pentanone is reacted with 2.3 g of 2,3,4,6-tetramethyl-benzene-sulfonic acid in 30 ml of ether until nitrogen no longer evolves. The reaction mixture is washed with water, dried and distilled in a vacuum to remove the ether. The residue is recrystallized from ethanol/water, affording 1.6 g of 2-oxopentyl-2,3,4,6-tetramethylbenzene sulfonate (Compound 95), m.p. 49° to 50° C. Yield 60.0%.

Workup

  1. washThe reaction mixture is washed with water
  2. customdried
  3. distillationdistilled in a vacuum
  4. customto remove the ether
  5. customThe residue is recrystallized from ethanol/water

Sources & evidence

ORD record
ord-9014d9fe19e9429a813a3c4d0e7cb5cf
Source dataset
uspto-grants-1984_12
Patent number
US04489091

Reaction notes

Loading…