Water → HCID 18918301, compound

HRID 864862Notes

Reaction equation

HRID 864862 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH:19]([CH3:26])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].O>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH:19]([CH3:26])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7638MonobenzoneHCID 24758Sodium hydrideHCID 95424Butanoic acid, 3-bromo-, ethyl ester

Product 1

HCID 18918301HCID 18918301, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-benzyloxyphenol (4.2 g) in dimethyl formamide (50 ml) was treated with sodium hydride (840 mg of a 60% dispersion), and the mixture stirred until evolution of gas ceased. There was then added ethyl 3-bromobutyrate (2.9 ml), and the solution stirred overnight. It was then poured into water (300 ml) and the mixture extracted with ether (3×50 ml). The combined extracts were washed with water (3×) and brine, dried (MgSO4) and evaporated to give a crude product as a brown oil (6 g). This was purified by chromatography on silica, eluting with hexane containing increasing amounts of ethyl acetate to give ethyl 3-(4-benzyloxyphenoxy)butyrate as a colourless crystalline solid (4.5 g) NMR (d6DMSO): δ1.25 (3H,t);1.8-2.0 (2H,m); 2.45 (2H,t); 3.9 (2H,t); 4.1 (2H,q); 5.0 (2H,s); 6.8-7.0 (4H,m); 7.4 (5H,m); m/e 314 (M+H)+.

Workup

  1. extractionthe mixture extracted with ether (3×50 ml)
  2. washThe combined extracts were washed with water (3×) and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give a crude product as a brown oil (6 g)
  6. customThis was purified by chromatography on silica
  7. washeluting with hexane containing
  8. temperatureincreasing amounts of ethyl acetate

Sources & evidence

ORD record
ord-946d0ceec07847dab9ee6753adffd4e6
Source dataset
uspto-grants-1996_10
Patent number
US05563141

Reaction notes

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