Pyridine → 1,4-Bis(benzoyloxymethyl)cyclohexane

HRID 132716

Reaction equation

HRID 132716 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][OH:10])[CH2:5][CH2:4]1.N1C=C[CH:14]=[CH:13][CH:12]=1.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[O:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1>>[C:17]([O:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][O:10][C:30](=[O:26])[C:29]2[CH:14]=[CH:13][CH:12]=[CH:27][CH:28]=2)[CH2:5][CH2:4]1)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 77351,4-CyclohexanedimethanolHCID 8028Tetrahydrofuran

Product 1

HCID 1182441,4-Bis(benzoyloxymethyl)cyclohexaneYield 95%

Procedure

To 0.03 mol 1,4-dihydroxymethylcyclohexane were added 30 ml tetrahydrofuran and 0.09 mol pyridine, then added 0.075 mol benzoyl chloride with stirring. The reaction was heated refluxing for 4 hours, cooled and added 20 ml saturated saline. The reaction mixture was extracted with ethyl acetate, and the extract was dried over anhydrous sodium sulfate, filtered. After removing solvent, the crude was purified by recrystallization from ethyl acetate and petroleum ether (2:1 v/v) to give 1,4-di(benzoyloxymethyl)cyclohexane as a white solid. The yield was 95%, and m.p. was 111-113° C.

Workup

  1. temperatureThe reaction was heated
  2. temperaturerefluxing for 4 hours
  3. temperaturecooled
  4. additionadded 20 ml saturated saline
  5. extractionThe reaction mixture was extracted with ethyl acetate
  6. dry with materialthe extract was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customAfter removing solvent
  9. customthe crude was purified by recrystallization from ethyl acetate and petroleum ether (2:1 v/v)

Sources & evidence

ORD record
ord-b5d3024eff4646769e9da25fb1b1ae6a
Source dataset
uspto-grants-2008_06
Patent number
US07388061B2

Linked notes

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