Hydrochloric Acid → 2-(Benzyloxy)-5-bromobenzoic acid

HRID 1623627Notes

Reaction equation

HRID 1623627 reaction equation
[Li+].[OH-].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:8]([CH:19]=1)[C:9]([O:11]CC1C=CC=CC=1)=[O:10].Cl>O1CCCC1.O>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:8]([CH:19]=1)[C:9]([OH:11])=[O:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 17750009Benzyl 2-(benzyloxy)-5-bromobenzoate

Product 1

HCID 24613572-(Benzyloxy)-5-bromobenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Solid LiOH (0.53 g, 12.59 mmol) was added to a stirred solution of phenylmethyl 5-bromo-2-[(phenylmethyl)oxy]benzoate (may be prepared as described in Description 4; 1 g, 2.52 mmol) in tetrahydrofuran (20 ml) and water (4.00 ml) in air at room temperature. The reaction mixture was stirred at 70° C. overnight. After cooling to room temperature, the solvent was removed to obtain a white solid, which was dissolved in water (100 ml) and stirred in ice-water bath. 1N HCl (aq) was added to adjust the pH to 4. The white solid was filtered and dried in vacuum to yield the title compound as a white solid. 0.78 g.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was removed
  3. customto obtain a white solid, which
  4. filtrationThe white solid was filtered
  5. customdried in vacuum

Sources & evidence

ORD record
ord-ab54ef6465c0425aa5137e9e2e7e0edf
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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