Methyl 2-[(3-bromophenoxy)methyl]benzoate → HCID 20085920, compound

HRID 2351117Notes

Reaction equation

HRID 2351117 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[O:5][CH2:6][C:7]1[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=1[C:9]([O:11]C)=[O:10]>[OH-].[Na+].CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[O:5][CH2:6][C:7]1[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=1[C:9]([OH:11])=[O:10]

Participants

4

Reactant 1

HCID 20085915Methyl 2-[(3-bromophenoxy)methyl]benzoate

Product 1

HCID 20085920HCID 20085920, compoundYield 107.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Methyl 2-(3-bromophenoxy)methylbenzoate (34 g) was refluxed in a mixture of 100 mL of 10% sodium hydroxide and 200 mL of methanol for 3 hours. The reaction mixture was concentrate under reduced pressure and water was added to the residue. The mixture was then acidified with concentrated hydrochloric acid. Extracting the acidic solution with ethyl acetate and then concentration of the organic layer gave the 2-(3-bromophenoxy)methyl benzoic acid (35 g) m.p. 158°-159° C. pmr (CDCL3) δ: 8.10 (m, 1H, H6), 6.84-7.74 (m, 7H, aromatic H), 6.16 (br s, 1H, CO2H), 5.49 (s, 2H, ArCH2O).

Workup

  1. concentrationThe reaction mixture was concentrate under reduced pressure and water
  2. additionwas added to the residue
  3. extractionExtracting the acidic solution with ethyl acetate

Sources & evidence

ORD record
ord-45c5b4fb850942a9829599e326319af9
Source dataset
uspto-grants-1989_10
Patent number
US04871865

Reaction notes

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