Citric Acid → HCID 21874666, compound

HRID 733000Notes

Reaction equation

HRID 733000 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=[O:6].CCN(CC)CC.C(O)(=O)[CH2:22][C:23]([CH2:28]C(O)=O)([C:25](O)=O)[OH:24].C1C[O:37][CH2:36]C1>C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>[C:23]([O:24][C:36]([O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=[O:6])=[O:37])([CH3:22])([CH3:25])[CH3:28]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 692653-Hydroxy-4-nitrobenzoic acid

Product 1

HCID 21874666HCID 21874666, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 90495Di-tert-butyl dicarbonateCatalyst

Procedure

A solution of 3-hydroxy-4-nitrobenzoic acid (1.83 g, 10 mmol) in THF (10 mL) was treated with Et3N (3.4 mL, 24 mmol) and di-tert-butyl dicarbonate (2.40 mL, 11 μmol) and stirred at room temperature for 16 h. The reaction mixture was poured into 10% citric acid solution (20 mL), extracted with EtOAc (2×10 mL), dried (MgSO4) and concentrated in vacuo to give the title compound (2.36 g, 83%) as a cream solid; IR νmax (Nujol)/cm−1 2985, 1772, 1717 and 1592; NMR δH (400 MHz, DMSO) 13.85 (1H, s), 8.26 (1H, d, J 8.5 Hz), 8.04 (1H, dd, J 8.5, 2.0 Hz), 7.98 (1H, d, J 2.0 Hz) and 1.49 (9H, s).

Workup

  1. extractionextracted with EtOAc (2×10 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-05b5288ad381410baf81d81c19f594db
Source dataset
uspto-grants-2009_09
Patent number
US07589097B2

Reaction notes

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