Hydrochloric Acid → Benzyl 2-benzyloxy-4-hydroxybenzoate

HRID 2220601Notes

Reaction equation

HRID 2220601 reaction equation
[OH-].[Na+].C([O:11][C:12]1[CH:27]=[CH:26][C:15]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])=[C:14]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:13]=1)(=O)C1C=CC=CC=1.Cl>CO>[CH2:29]([O:28][C:14]1[CH:13]=[C:12]([OH:11])[CH:27]=[CH:26][C:15]=1[C:16]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23090801Benzyl 4-benzoyloxy-2-benzyloxybenzoate

Product 1

HCID 23090785Benzyl 2-benzyloxy-4-hydroxybenzoateYield 40.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 2 mol/L aqueous solution of sodium hydroxide (6.39 mL) was added to a mixture of benzyl 4-benzoyloxy-2-benzyloxybenzoate (2.80 g) in methanol/tetrahydorofuran (1/1, 20 mL), and the mixture was stirred at room temperature for 5 hrs. To the reaction mixture was added 2 mol/L hydrochloric acid (6.39 mL). The solvent was evaporated under reduced pressure, and water was added to the residue. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium-pressure silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1) to afford benzyl 2-benzyloxy-4-hydroxybenzoate (0.859 g)

Workup

  1. customThe solvent was evaporated under reduced pressure, and water
  2. additionwas added to the residue
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by medium-pressure silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-a52ca05c3c6549e48e0dfeccc4ed3274
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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