Sodium Hydroxide → 2,4-Bis(benzyloxy)-5-bromobenzoic acid

HRID 1643335Notes

Reaction equation

HRID 1643335 reaction equation
[OH-].[Na+].[Br:3][C:4]1[C:5]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:6][C:7]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:8]([CH:13]=1)[C:9]([O:11]C)=[O:10]>C1COCC1>[Br:3][C:4]1[C:5]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:6][C:7]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:8]([CH:13]=1)[C:9]([OH:11])=[O:10]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59317108Methyl 5-bromo-2,4-dibenzyloxybenzoate

Product 1

HCID 469156382,4-Bis(benzyloxy)-5-bromobenzoic acidYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.3 800 ml of 2N NaOH are added to a solution of 150 g of methyl 5-bromo-2,4-dibenzyloxybenzoate in 500 ml of THF, and the mixture is stirred at 50° for 2 hours and subsequently stirred at room temperature for 16 hours. The red alkaline phase is separated off and cooled, and conc. hydrochloric acid is added dropwise to pH 2-3. The precipitated product is separated off and dried, giving 132 g of 5-bromo-2,4-dibenzyloxybenzoic acid.

Workup

  1. stirringsubsequently stirred at room temperature for 16 hours
  2. customThe red alkaline phase is separated off
  3. temperaturecooled
  4. additionconc. hydrochloric acid is added dropwise to pH 2-3
  5. customThe precipitated product is separated off
  6. customdried

Sources & evidence

ORD record
ord-f90b54a21b2b450a95db264c6c2a2c4b
Source dataset
uspto-grants-2012_02
Patent number
US08119795B2

Reaction notes

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