HCID 20085922, compound → HCID 20085919, compound

HRID 1463183Notes

Reaction equation

HRID 1463183 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=2)=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8]>[OH-].[Na+].CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=2)=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 1

HCID 20085922HCID 20085922, compound

Product 1

HCID 20085919HCID 20085919, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

Methyl 5-bromo-2-(4-bromophenoxymethyl)benzoate (90 g, 0.23 mole) 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 acidified with concentrated hydrochloric acid. A solid was precipitated and collected as the acid product (80 g). mp 214°-215° C. pmr (DMSO-d6) 6: 6.76-8.01 (m, 7H, aromatic H), 5.38 (s, 2H, ArCH2O).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and water
  2. additionwas added to the residue
  3. customA solid was precipitated
  4. customcollected as the acid product (80 g)

Sources & evidence

ORD record
ord-30a8b0d1a7764a94b8b3cb92c1415b52
Source dataset
uspto-grants-1994_04
Patent number
US05300282

Reaction notes

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