tert-Butanol → 2-Nitro-terephthalic acid 1-tert-butyl ester 4-methyl ester

HRID 1773396Notes

Reaction equation

HRID 1773396 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[C:6]([N+:13]([O-:15])=[O:14])[CH:5]=1.[C:17](O)([CH3:20])([CH3:19])[CH3:18].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:12]=[CH:11][C:7]([C:8]([O:10][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:9])=[C:6]([N+:13]([O-:15])=[O:14])[CH:5]=1

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 90495Di-tert-butyl dicarbonateHCID 219064744-(Methoxycarbonyl)-2-nitrobenzoic acid

Product 1

HCID 675127822-Nitro-terephthalic acid 1-tert-butyl ester 4-methyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Commercially available 2-nitro-terephthalic acid 4-methyl ester (4.84 g, 21.49 mmol) in DCM (54 mL) was treated with tert-butanol (4.05 mL, 42.99 mmol), di-tert-butyl dicarbonate (12.19 g, 55.87 g) and DMAP (0.79 g, 6.45 mmol). After 4 days at room temperature, the reaction was diluted with DCM (100 mL), washed with 1N HCl (100 mL), aqueous NaHCO3 and finally with water. After drying over sodium sulphate and evaporation of the volatiles, the title compound was obtained as a brownish oil in more than quantitative yield (6.51 g). The crude was employed in the following step with no further purification.

Workup

  1. washwashed with 1N HCl (100 mL), aqueous NaHCO3 and finally with water
  2. dry with materialAfter drying over sodium sulphate and evaporation of the volatiles

Sources & evidence

ORD record
ord-1852d564dc654105a9f5f93407a8e857
Source dataset
uspto-grants-2016_02
Patent number
US09255087B2

Reaction notes

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