Water → Benzoic acid, 3-nitrophenyl ester

HRID 1841840Notes

Reaction equation

HRID 1841840 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C(N(CC)CC)C.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>ClCCl>[C:18]([O:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 111373-Nitrophenol

Product 1

HCID 2749920Benzoic acid, 3-nitrophenyl esterYield 90.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Nitrophenol (1.716 g, 12.346 mmol) and triethylamine (1.6 mL, 12.346 mmol) were dissolved in 50 mL of dichloromethane. The solution was shaken 30 minutes at room temperature. Benzoyl chloride (1.43 mL, 12.346 mmol) was added drop by drop and the resulting solution was shaken at room temperature until full conversion as determined by thin-layer chromatography. Carbonated water (20 mL) was added three times. The organic phase was dried over magnesium sulfate, filtered and the solvent was removed under reduced pressure, thus affording 2.7080 g of a white solid corresponding to 3-nitrophenyl benzoate (11.144 mmol, yield=90%).

Workup

  1. stirringthe resulting solution was shaken at room temperature until full conversion
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-746948d6ac4a4c8eade3027451cd2569
Source dataset
uspto-grants-2015_02
Patent number
US08945522B2

Reaction notes

Loading…