Hydrochloric Acid → 5-(9-Carboxy-nonyloxy)-isophthalic Acid Di-tert-butyl Ester

HRID 1022417Notes

Reaction equation

HRID 1022417 reaction equation
[C:1]([O:5][C:6](=[O:34])[C:7]1[CH:19]=[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32]C)=[O:31])[CH:17]=[C:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].CCOC(C)=O.Cl>C1COCC1>[C:1]([O:5][C:6](=[O:34])[C:7]1[CH:19]=[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])[CH:17]=[C:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:8]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 684414955-(9-Methoxycarbonyl-nonyloxy)-isophthalic Acid Di-tert-butyl Ester

Product 1

HCID 684432455-(9-Carboxy-nonyloxy)-isophthalic Acid Di-tert-butyl Ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(9-methoxycarbonyl-nonyloxy)-isophthalic acid di-tert-butyl ester (162 mg, 0.34 mmol) in THF (2 ml) was added 1 N NaOH (0.35 ml). The mixture was refluxed for 7 h. The mixture was left at room temperature over night before concentration. To the residue EtOAc and 0.1N HCl was added. The aqueous layer was extracted twice with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated to give a clear syrup.

Workup

  1. temperatureThe mixture was refluxed for 7 h
  2. waitThe mixture was left at room temperature over night before concentration
  3. extractionThe aqueous layer was extracted twice with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto give a clear syrup

Sources & evidence

ORD record
ord-b19fc40af234415eaf4c55837b010900
Source dataset
uspto-grants-2014_05
Patent number
US08722620B2

Reaction notes

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