Dichloromethane → 3-Nitro-5-(octadecyloxy)benzoic acid methyl ester

HRID 488272Notes

Reaction equation

HRID 488272 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[C:6]([OH:13])[CH:5]=1.Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>CN(C=O)C>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:5]=[C:6]([O:13][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH3:16])[CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 82181-BromooctadecaneHCID 11430Potassium CarbonateHCID 239344Methyl 3-hydroxy-5-nitrobenzoate

Product 1

HCID 536989543-Nitro-5-(octadecyloxy)benzoic acid methyl esterYield 92.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.7 g (8.6 mmol) of 3-hydroxy-5-nitrobenzoic acid methyl ester [prepared as described by D. J. Abraham, D. M. Gazze, P. E. Kennedy and M. Mokotoff, J. Med. Chem. 27, 1549 (1984)], 3.2 g (9.5 mmol) of 1-bromooctadecane and 1.8 g (12.9 mmol) of potassium carbonate in 35 ml of anhydrous DMF was stirred and heated at 75° for 25 hours. After cooling, 150 ml of methylene chloride was added and the insoluble salts were removed by filtration. The filtrate was concentrated at reduced pressure to a solid which was purified by HPLC using 30% methylene chloridehexane to give 3.57 g (92% yield, mp 64°-66°) of 3-nitro-5-(octadecyloxy)benzoic acid methyl ester.

Workup

  1. temperatureheated at 75° for 25 hours
  2. temperatureAfter cooling
  3. customthe insoluble salts were removed by filtration
  4. concentrationThe filtrate was concentrated at reduced pressure to a solid which
  5. customwas purified by HPLC

Sources & evidence

ORD record
ord-9feecebd59444d478b7d05c1c12f6e43
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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