Hydrochloric Acid → HCID 22914708, compound

HRID 1377678Notes

Reaction equation

HRID 1377678 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]([O:16]C)=[O:15])=[C:10]([O:18][CH3:19])[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Na+].Cl>C1COCC1>[C:1]([O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[C:10]([O:18][CH3:19])[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 22914723HCID 22914723, compound

Product 1

HCID 22914708HCID 22914708, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(t-Butyloxycarbonyl)-1 -methoxycarbonyl-2-methoxybenzene (770 mg, 2.9 mmol) from Step 3 was dissolved in 1:1 THF:H2O (10 mL) and to the solution was added 1N NaOH (4 mL, 4 mmol). After being stirred at ambient temperature for 24 h, the solution was acidified to pH 2 with 1N HCl and the solvents were removed under reduced pressure. The residue was dissolved in CHCl3 and washed with water. The CHCl3 layer was dried (MgSO4), filtered, and evaporated under reduced pressure to give 4-(t-butyloxycarbonyl)-2-methoxybenzene 1-carboxylic acid as a white solid (86% yield).

Workup

  1. customthe solvents were removed under reduced pressure
  2. dissolutionThe residue was dissolved in CHCl3
  3. washwashed with water
  4. dry with materialThe CHCl3 layer was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-030ab5278ebb4b7581d7cb5652e3b7ee
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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