Dimethylformamide → HCID 178460355, compound

HRID 355485Notes

Reaction equation

HRID 355485 reaction equation
CN(C)C=O.[CH2:6]([C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)[CH3:7].C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][CH2:29][CH2:30][OH:31]>C(OCC)(=O)C.O>[CH2:6]([C@H:8]1[CH2:9][CH2:10][C@H:11]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH:30]([OH:31])[CH2:29][CH3:28])=[CH:18][CH:19]=2)[CH2:12][CH2:13]1)[CH3:7]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 178455720HCID 178455720, compound

Product 1

HCID 178460355HCID 178460355, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 1-liter three-necked flask equipped with a condenser and a stirrer were placed 500 ml of dimethylformamide, 20.4 g (0.10 mol) of 4-(trans-4-ethyl-cyclohexyl)phenol and 41.4 g (0.30 mol) of potassium carbonate, followed by stirring at room temperature. Afterward, 18.1 g (0.13 mol) of 3-bromo-1-propanol was added thereto, and the solution was then vigorously stirred at 100° C. After reaction for 10 hours, this solution was poured into 2 liters 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 2N aqueous sodium hydroxide 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 n-heptane twice to obtain 17.6 g (0.067 mol) of 4-(trans-4-ethyl-cyclohexyl)phenoxypropanol. Its melting point was in the range of 68.5° to 69.9° C.

Workup

  1. customIn a 1-liter three-necked flask equipped with a condenser and a stirrer
  2. stirringthe solution was then vigorously stirred at 100° C
  3. customAfter reaction for 10 hours
  4. washIn succession, the resultant organic layer was washed with 3N hydrochloric acid three times
  5. dry with materialThe resultant ethyl acetate layer was dried over anhydrous sodium sulfate
  6. distillationthe solvent was then distilled off under reduced pressure
  7. customNext, the resultant crystal was recrystallized from n-heptane twice

Sources & evidence

ORD record
ord-6c712a2f2bb845af9c5cc33ee7012671
Source dataset
uspto-grants-1998_11
Patent number
US05830976

Reaction notes

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