Pyridine → 1,4-Bis(benzoyloxymethyl)cyclohexane

HRID 132716

反応式

HRID 132716 の反応式
[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

参加物

5

反応物 4

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

生成物 1

HCID 1182441,4-Bis(benzoyloxymethyl)cyclohexane収率 95%

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b5d3024eff4646769e9da25fb1b1ae6a
出典データセット
uspto-grants-2008_06
特許番号
US07388061B2

関連ノート

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