Epibromohydrin → 2-{2-[4-(2-Methoxyphenyl)butyl]phenoxymethyl}oxirane

HRID 743196Notes

Reaction equation

HRID 743196 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19].[CH3:20][C:21](C)([O-:23])[CH3:22].[K+].C(C1OC1)Br>CC(N(C)C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH2:20][CH:21]1[CH2:22][O:23]1

Participants

5

Reactant 3

HCID 18430EpibromohydrinHCID 194239792-[4-(2-Methoxyphenyl)butyl]phenolHCID 23665647Potassium tert-butoxide

Product 1

HCID 106388632-{2-[4-(2-Methoxyphenyl)butyl]phenoxymethyl}oxiraneYield 93%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Following a procedure similar to that described in Example 1(a), 230 mg of 2-[4-(2-methoxyphenyl)butyl]phenol (prepared as described in Preparation 4), 101 mg of potassium t-butoxide and 246 mg of epibromohydrin were reacted in 15 ml of dimethylacetamide. The crude product, extracted as described in Example 1(a), was purified as described in Example 1(a), to give 260 mg (yield 93%) of the title compound as an oil.

Workup

  1. extractionThe crude product, extracted
  2. customwas purified

Sources & evidence

ORD record
ord-26eb422a15f1495bbb522969fe987898
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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