Sulfuric Acid → HCID 22311653, compound

HRID 965599Notes

Reaction equation

HRID 965599 reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].S(=O)(=O)(O)O.[CH:22]1([CH2:28][CH2:29]O)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.S1(CCCC1)(=O)=O>CO>[Cl:1][C:2]1[C:3]([N+:14]([O-:16])=[O:15])=[CH:4][C:5]([C:6]([O:8][CH2:29][CH2:28][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[O:7])=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 83774-Chloro-3,5-dinitrobenzoic acid2×HCID 205082-CyclohexylethanolHCID 31347Sulfolane

Product 1

HCID 22311653HCID 22311653, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
105 °C

Procedure

After charging 50 parts of 4-chloro-3,5-dinitrobenzoic acid, 0.3 part of 98% sulfuric acid, 78 parts of cyclohexaneethanol and 50 parts of sulfolane into a flask, the mixture was heated to 100 to 110° C., and was maintained at the same temperature for 8 to 10 hours. After checking the disapearance of 4-chloro-3,5-dinitrobenzoic acid by HPLC, the reaction mass was cooled to room temperature under atmospheric pressure, and to the mass was 240 parts of methanol, and was stirred for 30 minutes. The resulting mixture was filtrated to obtain crystals, and the crystals were washed with 40 parts of methanol and then dried to obtain 58 parts of 2-cyclohexylethyl 4-chloro-3,5-dinitrobenzoate.

Workup

  1. temperaturewas maintained at the same temperature for 8 to 10 hours
  2. temperaturethe reaction mass was cooled to room temperature under atmospheric pressure
  3. filtrationThe resulting mixture was filtrated
  4. customto obtain crystals
  5. washthe crystals were washed with 40 parts of methanol
  6. customdried

Sources & evidence

ORD record
ord-76d68e3b06264d01ba5acf5412e76e48
Source dataset
uspto-grants-2005_10
Patent number
US06951706B2

Reaction notes

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