Water → HCID 178455723, compound

HRID 355486Notes

Reaction equation

HRID 355486 reaction equation
[CH2:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]2[CH:19]=[CH:18][C:12]([O:13][CH:14](O)[CH2:15][CH3:16])=[CH:11][CH:10]=2)[CH2:5][CH2:4]1)[CH3:2].C(N(CC)CC)C.[N+:27]([C:30]1[CH:31]=[C:32]([CH:36]=[C:37]([N+:39]([O-:41])=[O:40])[CH:38]=1)[C:33](Cl)=[O:34])([O-:29])=[O:28].[OH2:42]>C1COCC1.C(OCC)(=O)C>[N+:27]([C:30]1[CH:31]=[C:32]([CH:36]=[C:37]([N+:39]([O-:41])=[O:40])[CH:38]=1)[C:33]([O:42][CH2:16][CH2:15][CH2:14][O:13][C:12]1[CH:18]=[CH:19][C:9]([C@H:6]2[CH2:7][CH2:8][C@H:3]([CH2:1][CH3:2])[CH2:4][CH2:5]2)=[CH:10][CH:11]=1)=[O:34])([O-:29])=[O:28]

Participants

7

Reactant 4

HCID 962WaterHCID 74323,5-Dinitrobenzoyl chlorideHCID 8471TriethylamineHCID 178460355HCID 178460355, compound

Product 1

HCID 178455723HCID 178455723, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

In a 500-ml three-necked flask equipped with a stirrer was placed 300 ml of THF, and 18.0 g (0.068 mol) of 4-(trans-4-ethyl-cyclohexyl)phenoxypropanol obtained in the above-mentioned manner and 11.4 ml of triethylamine were added, followed by stirring at 0° C. Afterward, a solution obtained by dissolving 15.7 g (0.068 mol) of 3,5-dinitrobenzoyl chloride in 50 ml of THF was added dropwise to the flask over 30 minutes, and under this state, reaction was carried out for 6 hours. After the completion of the reaction, this solution was poured into 1 liter of water, and extraction was then made with 1.5 liters of ethyl acetate. In succession, the resultant organic layer was washed with 3N hydrochloric acid three times, a saturated sodium bicarbonate solution three times and water. The resultant ethyl acetate layer was dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. Next, the resultant crystal was recrystallized from ethyl acetate twice to obtain 23.3 g (0.051 mol) of [4-(trans-4-ethyl-cyclohexyl)phenoxypropyl] 3,5-dinitrobenzoate. Its melting point was in the range of 108.0° to 109.4° C. The structure of this compound was confirmed by IR and NMR.

Workup

  1. customIn a 500-ml three-necked flask equipped with a stirrer
  2. additionwere added
  3. customAfterward, a solution obtained
  4. additionwas added dropwise to the flask over 30 minutes
  5. customunder this state, reaction
  6. customAfter the completion of the reaction
  7. washIn succession, the resultant organic layer was washed with 3N hydrochloric acid three times
  8. dry with materialThe resultant ethyl acetate layer was dried over anhydrous sodium sulfate
  9. distillationthe solvent was then distilled off under reduced pressure
  10. customNext, the resultant crystal was recrystallized from ethyl acetate twice

Sources & evidence

ORD record
ord-15adc121f2fa4d159781924a97dd652f
Source dataset
uspto-grants-1998_11
Patent number
US05830976

Reaction notes

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