Hydrochloric Acid → 1-(4-Bromophenyl)-2-nitro-1,3-diacetoxypropane

HRID 2417628Notes

Reaction equation

HRID 2417628 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[N+:10]([CH:13](O)[CH3:14])([O-:12])=[O:11].Cl.[C:17]([O:20]C(=O)C)(=[O:19])[CH3:18].[C:24](Cl)(=[O:26])[CH3:25]>CCOCC.O.C(N(CC)CC)C.CO>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([O:7][C:24](=[O:26])[CH3:25])[CH:13]([N+:10]([O-:12])=[O:11])[CH2:14][O:20][C:17](=[O:19])[CH3:18])=[CH:4][CH:3]=1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 7918Acetic AnhydrideHCID 707414-BromobenzaldehydeHCID 22056827Nitroethanol

Product 1

HCID 134688951-(4-Bromophenyl)-2-nitro-1,3-diacetoxypropaneYield 79%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
-3 °C

Procedure

A mixture of 18.5 g (0.1 moles) of p-bromobenzaldehyde, 20 ml of methanol and 0.5 ml of triethylamine is cooled to -3° C., and 9.1 g (0.1 moles) of nitroethanol are added within one hour. The reaction mixture is stirred for 4 hours at 0°-5° C. 50 ml of water are added to the mixture, the mixture is cooled to 5° C., 30 ml of 0.5 n hydrochloric acid are added, and the mixture is stirred for 10 minutes. Thereafter 30 ml of ether are added to the mixture, the phases are separated from each other, and the etheral phase is evaporated. 30 g (0.29 moles) of acetic anhydride and 2 ml of acetyl chloride are added to the residue, the mixture is stirred at 60° C. for 2 hours, thereafter it is poured onto 100 g of ice and stirred for 3 hours. The separated product is filtered off. 28.7 g (79%) of the title compound are obtained; m.p.: 81°-82° C. According to thin layer chromatography the product is uniform; Rf =0.76 (solvent: a 90:10:1 mixture of benzene, methanol and acetone).

Workup

  1. temperaturethe mixture is cooled to 5° C.
  2. stirringthe mixture is stirred for 10 minutes
  3. customthe phases are separated from each other, and the etheral phase
  4. customis evaporated
  5. stirringthe mixture is stirred at 60° C. for 2 hours
  6. stirringstirred for 3 hours
  7. filtrationThe separated product is filtered off

Sources & evidence

ORD record
ord-0da6b10105f84786b8bd67bb8b7b2126
Source dataset
uspto-grants-1984_09
Patent number
US04469703

Reaction notes

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