Diethyl Ether → 3,5-Bis(benzyloxy)-4-bromobenzoic acid

HRID 1643665Notes

Reaction equation

HRID 1643665 reaction equation
C([O:8][C:9](=[O:33])[C:10]1[CH:15]=[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:13]([Br:24])=[C:12]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:11]=1)C1C=CC=CC=1.[OH-].[Na+].CCOCC>C1COCC1.O>[CH2:17]([O:16][C:14]1[CH:15]=[C:10]([CH:11]=[C:12]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:13]=1[Br:24])[C:9]([OH:33])=[O:8])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 10051813Benzyl 3,5-bis(benzyloxy)-4-bromobenzoate

Product 1

HCID 100247103,5-Bis(benzyloxy)-4-bromobenzoic acidYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3,5-bis-benzyloxy-4-bromo-benzoic acid benzyl ester (200a) (225 g, 0.45 mol) in THF (400 mL) and H2O (500 mL) was added NaOH (89.4 g, 2.24 mol) in one portion. The mixture was refluxed for 4 hr. TLC (EtOAc/petroleum ether=1/4) showed that the reaction was complete. Et2O (100 mL) was added to the mixture and the organic layer was separated. The aqueous layer was acidified with conc. HCl, and the resulting solid was filtered and dried in vacuo to give the title compound (150 g, 85% yield) as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.48 (dd, 4H), 7.39(t, 4H), 7.31 (m, 4H), 5.27(s, 4H).

Workup

  1. temperatureThe mixture was refluxed for 4 hr
  2. customthe organic layer was separated
  3. filtrationthe resulting solid was filtered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-7a0603be134f48f0a54254b6c4a84e8c
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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