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

HRID 1463177Notes

Reaction equation

HRID 1463177 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-bromophenoxymethyl)benzoate (34 g) was refluxed in a mixture of 100 mL of 10% sodium hydroxide and 200 mL of methanol for three 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 2-(3-bromophenoxymethyl) benzoic acid (35 g) m.p. 158°-159° C. pmr (CDCL3) 6: 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-44c71ac7c1b54a0fbe9ed225cc57efae
Source dataset
uspto-grants-1994_04
Patent number
US05300282

Reaction notes

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