Bromomethyl 4-methoxyphenyl ketone → 2-Hydroxy-1-(4-methoxyphenyl)ethanone

HRID 1034134Notes

Reaction equation

HRID 1034134 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=[O:4].CN1CCCC1=[O:19]>O>[OH:19][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 4965Bromomethyl 4-methoxyphenyl ketone2×HCID 13387N-methyl-2-pyrrolidone

Product 1

HCID 777862-Hydroxy-1-(4-methoxyphenyl)ethanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

It is used in the synthesis of MOPMN, above, and was synthesized from 2-bromo-4'-methoxyacetophenone (Aldrich). The 2-bromo-4'-methoxyacetophenone was refluxed in 20% water and N-methyl-2-pyrrolidinone for 10 hours at 105° C. The product was extracted with ethylether, dried over MgSO4, the ether evaporated and the dry solid recrystallized before use. Melting point 98.5°-100.5° C. and the NMR corresponds to the product.

Workup

  1. customIt is used in the synthesis of MOPMN
  2. extractionThe product was extracted with ethylether
  3. dry with materialdried over MgSO4
  4. customthe ether evaporated
  5. customthe dry solid recrystallized before use

Sources & evidence

ORD record
ord-ebc5830933c54250a851bf8a2fd0df97
Source dataset
uspto-grants-1994_05
Patent number
US05314815

Reaction notes

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