Hydrochloric Acid → 2,4-Bis(benzyloxy)-5-bromobenzoic acid

HRID 2410250Notes

Reaction equation

HRID 2410250 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]([Br:27])=[CH:15][C:10]=1[C:11]([O:13]C)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C1COCC1.O>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]([Br:27])=[CH:15][C:10]=1[C:11]([OH:13])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59317108Methyl 5-bromo-2,4-dibenzyloxybenzoate

Product 1

HCID 469156382,4-Bis(benzyloxy)-5-bromobenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
68 °C

Procedure

6.4 kg of methyl 2,4-bisbenzyloxy-5-bromobenzoate in 18 l of THF are added to a solution of 3 kg of sodium hydroxide in 30 l of water. After stirring overnight at 68° C., the mixture is cooled to 10° C., and 7.5 l of HCl (w: 37%) are added via a dropping funnel (pH 1). The mixture is stirred for a further 1 h and subsequently filtered. The residue is dried to constant weight in vacuo at 60° C.; 5.687 kg (91%) of 2,4-bisbenzyloxy-5-bromo-benzoic acid (m.p. 150-152° C.; MW 413.3).

Workup

  1. temperaturethe mixture is cooled to 10° C.
  2. stirringThe mixture is stirred for a further 1 h
  3. filtrationsubsequently filtered
  4. customThe residue is dried to constant weight in vacuo at 60° C.

Sources & evidence

ORD record
ord-feda1c8082674573b1b3b9c6a1b59b80
Source dataset
uspto-grants-2014_08
Patent number
US08816070B2

Reaction notes

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