Bromomethyl 4-methoxyphenyl ketone → 1-(2-Bromo-1,1-diethoxyethyl)-4-methoxybenzene

HRID 1253314Notes

Reaction equation

HRID 1253314 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=[O:4].C(OCC)(OCC)O[CH2:15][CH3:16].[CH3:23]S(O)(=O)=O.[C:28](=[O:31])([O-])[O-].[Na+].[Na+]>C(O)C>[Br:1][CH2:2][C:3]([O:31][CH2:28][CH3:23])([O:4][CH2:15][CH3:16])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 6395Methanesulfonic AcidHCID 10340Sodium CarbonateHCID 31214Ethyl orthoformate

Product 1

HCID 155798781-(2-Bromo-1,1-diethoxyethyl)-4-methoxybenzeneYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-bromo-1-(4'-methoxy-phenyl)-ethanone (5 g, 22 mmol), triethyl orthoformate (9 g, 61 mmol), methanesulfonic acid (0.3 g, 3.1 mmol) and ethanol (20 ml) is kept at 40° C. for 3 h. The solution is poured, under vigorous stirring, into a saturated sodium carbonate solution (0.2 l) and extracted with ethyl ether (3×50 ml). The combined organic extract is washed with a 2% sodium hydrogen carbonate solution. Evaporation of the solvent in vacuo leaves an oil, which is crystallized from methanol to give 2-bromo-1,1-diethoxy-1-(4'-methoxy-phenyl)-ethane (5 g, 16 mmol, yield: 73%) as analytically pure product.

Workup

  1. extractionextracted with ethyl ether (3×50 ml)
  2. extractionThe combined organic extract
  3. washis washed with a 2% sodium hydrogen carbonate solution
  4. customEvaporation of the solvent in vacuo
  5. customleaves an oil, which
  6. customis crystallized from methanol

Sources & evidence

ORD record
ord-2abaa409cea243b8acde78f6a08a9430
Source dataset
uspto-grants-1988_05
Patent number
US04748253

Reaction notes

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