2-Nitrophenol → HCID 68901063, compound

HRID 2308271Notes

Reaction equation

HRID 2308271 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].[CH3:11][O:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([C:21](Cl)=[O:22])=[CH:17][CH:16]=1)=[O:14]>C1COCC1.N1C=CC=CC=1.C(=O)(O)[O-].[Na+].CCOC(C)=O>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][C:21](=[O:22])[C:18]1[CH:17]=[CH:16][C:15]([C:13]([O:12][CH3:11])=[O:14])=[CH:20][CH:19]=1)([O-:3])=[O:2]

Participants

7

Reactant 2

HCID 69472-NitrophenolHCID 81850Methyl 4-(chlorocarbonyl)benzoate

Product 1

HCID 68901063HCID 68901063, compoundYield 94%

Reagents, catalysts & solvents 4

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 2-nitrophenol (1.55 g, 11.2 mmol) and methyl 4-chlorocarbonyl benzoate (2.44 g, 12.2 mmol) in THF (14 mL) and pyridine (2.8 mL) was stirred for 2 h at room temperature. The reaction was diluted with saturated sodium bicarbonate (30 mL) and EtOAc (20 mL), the phases separated and the aqueous phase extracted with EtOAc (2×15 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure to afford terephthalic acid 1-methyl ester 4-(2-nitrophenyl) ester (3.15 g, 94%). 1H NMR (CDCl3) δ 3.98 (s, 3H), 7.43 (d, 1H, J=7.8 Hz), 7.48 (t, 1H, J=7.8 Hz), 7.73 (t, 1H, J=7.8 Hz), 8.20 (m, 4H), 8.27 (m, 1H).

Workup

  1. customthe phases separated
  2. extractionthe aqueous phase extracted with EtOAc (2×15 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-92beb967958941578cc7491e4dae535c
Source dataset
uspto-grants-2004_12
Patent number
US06835731B2

Reaction notes

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