Water → Methyl 2-[1-(3-chlorophenoxy)ethyl]benzoate

HRID 1493494Notes

Reaction equation

HRID 1493494 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Br[CH:12]([C:14]1[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17])[CH3:13].O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH:12]([C:14]1[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 79333-ChlorophenolHCID 24758Sodium hydrideHCID 15870654Methyl 2-(1-bromoethyl)benzoate

Product 1

HCID 18764887Methyl 2-[1-(3-chlorophenoxy)ethyl]benzoateYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 3-chlorophenol (8.2 g) in DMF (30 ml) was added dropwise to a stirred suspension of sodium hydride (1.3 g) in DMF (30 ml). An hour later, a solution of crude methyl 2-(1-bromoethyl)benzoate described above (12 g) in DMF was added with stirring. After stirring at room temperature for 2 hours, the resulting mixture was poured into water and extracted with ether. The ether extracts were washed successively with water (×2), aqueous sodium hydroxide (×2), and brine, then dried and concentrated to give methyl 2-[1-(3-chlorophenoxy)ethyl]benzoate (14.84 g, 88% pure by GC), as a yellow oil.

Workup

  1. customAn hour
  2. additionwas added
  3. stirringAfter stirring at room temperature for 2 hours
  4. extractionextracted with ether
  5. washThe ether extracts were washed successively with water (×2), aqueous sodium hydroxide (×2), and brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6bd1d168a9334d869e90a41678601b53
Source dataset
uspto-grants-1991_06
Patent number
US05021581

Reaction notes

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