Methanesulfonic Acid → HCID 13746078, compound

HRID 2290930Notes

Reaction equation

HRID 2290930 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([CH3:11])=[CH:5][C:4]=1[CH2:12][CH2:13][CH2:14][C:15]([OH:17])=O.CS(O)(=O)=O>>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([CH3:11])=[C:5]2[C:4]=1[CH2:12][CH2:13][CH2:14][C:15]2=[O:17]

Participants

3

Reactant 2

HCID 6395Methanesulfonic AcidHCID 20230748HCID 20230748, compound

Product 1

HCID 13746078HCID 13746078, compoundYield 44%

Procedure

A mixture of 4-(2,3-dimethoxy-5-methylphenyl)butyric acid (50.7 g, 0.21 mole) and methanesulfonic acid (507 g, 355 mL) was stirred at 0° for 1 hour and overnight at room temperature. The reaction mixture was poured onto ice, and the solution was extracted with CH2Cl2. The combined CH2Cl2 layers were washed with 1N KOH, water, saturated aqueous NaCl, dried (MgSO4), filtered, and evaporated to yield 20.2 g tan solid, (44%); mp 58°-62°; M+ 204.

Workup

  1. additionThe reaction mixture was poured onto ice
  2. extractionthe solution was extracted with CH2Cl2
  3. washThe combined CH2Cl2 layers were washed with 1N KOH, water, saturated aqueous NaCl
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-55f9b52e294940959f5b633ffff892af
Source dataset
uspto-grants-1986_10
Patent number
US04618683

Reaction notes

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