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

HRID 1650226Notes

Reaction equation

HRID 1650226 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 concentrated 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)methylbenzoic 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 concentrated under reduced pressure and water
  2. additionwas added to the residue
  3. extractionExtracting the acidic solution with ethyl acetate

Sources & evidence

ORD record
ord-905b84ebfb914c4795f2fdbb3785fc26
Source dataset
uspto-grants-1990_05
Patent number
US04923892

Reaction notes

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