Iodine → 2-Cyclohexene-1,4-dicarboxylic acid

HRID 385217ノート

反応式

HRID 385217 の反応式
[C:1]([OH:10])(=[O:9])/[CH:2]=[CH:3]\[CH:4]=[CH:5]\[C:6]([OH:8])=[O:7].II.[CH2:13]1COC[CH2:14]1>>[CH:2]1([C:1]([OH:10])=[O:9])[CH2:14][CH2:13][CH:5]([C:6]([OH:8])=[O:7])[CH:4]=[CH:3]1

参加物

4

反応物 3

HCID 807IodineHCID 8028TetrahydrofuranHCID 5280614(2E,4Z)-2,4-Hexadienedioic acid

生成物 1

HCID 3162142-Cyclohexene-1,4-dicarboxylic acid収率 75%

反応条件

温度
160 °C

実験手順

In a Parr reactor, a mixture of cis,trans muconic acid (8.18 g, 57.6 mmol), I2 (293 mg, 1.15 mmol, 2.0 mole percent), and THF (120 ml, 0.48 M) is heated to 160° C. for 25 hours under ethylene pressure (pRT=252 psi (1.74 MPa)). After cooling to room temperature, a white solid is found to be suspended in a weakly yellow solution. The solution is filtered to remove the precipitated trans,trans muconic acid and all solvent is evaporated on a rotary evaporator. The residue is suspended in hot ethyl acetate/dioxane; after cooling to room temperature, the precipitated solid is removed by filtration and the filtrate is evaporated to dryness to yield cyclohex-2-ene-1,4-dicarboxylic acid (7.22 g, 42.4 mmol, 75 percent).

後処理

  1. temperatureAfter cooling to room temperature
  2. filtrationThe solution is filtered
  3. customto remove the precipitated trans,trans muconic acid
  4. customall solvent is evaporated on a rotary evaporator
  5. temperatureafter cooling to room temperature
  6. customthe precipitated solid is removed by filtration
  7. customthe filtrate is evaporated to dryness

出典と根拠

ORDレコード
ord-dceece6f5806425cb9dbaecaa0afcfed
出典データセット
uspto-grants-2013_02
特許番号
US08367859B2

反応ノート

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