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

HRID 1623624Notes

Reaction equation

HRID 1623624 reaction equation
O[Li].O.[Br:4][C:5]1[CH:6]=[CH:7][C:8]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:9]([CH:20]=1)[C:10]([O:12]CC1C=CC=CC=1)=[O:11].Cl>C1COCC1.O.C(OCC)(=O)C>[Br:4][C:5]1[CH:6]=[CH:7][C:8]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:9]([CH:20]=1)[C:10]([OH:12])=[O:11]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 17750009Benzyl 2-(benzyloxy)-5-bromobenzoate

Product 1

HCID 24613572-(Benzyloxy)-5-bromobenzoic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

LiOH.H2O (222 mg, 5.29 mmol) was added to a stirred solution of phenylmethyl 5-bromo-2-[(phenylmethyl)oxy]benzoate (may be prepared as described in Description 4, method A; 700 mg, 1.76 mmol) in THF (15 ml) and water (5.00 ml). The mixture was refluxed for 12 h and then diluted with ethyl acetate (50 ml). 10% aqueous HCl was added to the mixture to adjust the pH to 2. The organic phase was isolated, washed with brine, dried over MgSO4, and concentrated to yield the title compound as a yellow solid. 400 mg.

Workup

  1. temperatureThe mixture was refluxed for 12 h
  2. customThe organic phase was isolated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a7a97ca2c87d4435a50cd2e3f59aa95b
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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