L-Methionine → 4'-Hydroxyacetophenone

HRID 1460731Notes

Reaction equation

HRID 1460731 reaction equation
CS(O)(=O)=O.FC(F)(F)S(O)(=O)=O.N[C@H](C(O)=O)CCSC.C[O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31](=[O:33])[CH3:32])=[CH:27][CH:26]=1>>[OH:24][C:25]1[CH:30]=[CH:29][C:28]([C:31](=[O:33])[CH3:32])=[CH:27][CH:26]=1

Participants

5

Reactant 4

HCID 6137L-MethionineHCID 6395Methanesulfonic AcidHCID 74764'-MethoxyacetophenoneHCID 62406Trifluoromethanesulfonic acid

Product 1

HCID 74694'-HydroxyacetophenoneYield 30%

Procedure

In this connection, the demethylation of compounds of relatively simple structure by means of a couple sulfonic acid/derivative of the sulfide type, for instance methanesulfonic acid or trifluoromethanesulfonic acid and methionine, is known. This method is reported in particular in J. C. S. Perkin I. pp. 2288-2289 (1977). The results obtained with this method are usually very varied (yield of demethylated compounds varies from 30 to 90%) and may be poor. This is the case for p-methoxyacetophenone: no reaction is recorded at 20° C. and only 30% yield of p-hydroxyacetophenone is obtained after 72 hours at 60° C.

Workup

  1. customThe results obtained with this method
  2. customis recorded at 20° C.

Sources & evidence

ORD record
ord-9511f548ba004a60ad4ac4d43947c72a
Source dataset
uspto-grants-1991_12
Patent number
US05071985

Reaction notes

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