Sodium Carbonate → HCID 178444516, Verbindung

HRID 370371Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 370371
C(Cl)(=O)C(Cl)=O.[CH2:7]([C@H:12]1[CH2:17][CH2:16][C@H:15]([C@H:18]2[CH2:23][CH2:22][C@H:21]([C:24]([OH:26])=[O:25])[CH2:20][CH2:19]2)[CH2:14][CH2:13]1)[CH2:8][CH2:9][CH2:10][CH3:11].[CH2:27]([C:30]1[CH:35]=[CH:34][C:33]([C@H:36]2[CH2:41][CH2:40][C@H:39](O)[CH2:38][CH2:37]2)=[CH:32][CH:31]=1)[CH2:28][CH3:29].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.N1C=CC=CC=1.CN(C)C=O>[CH2:27]([C:30]1[CH:31]=[CH:32][C:33]([C@H:36]2[CH2:41][CH2:40][C@H:39]([O:25][C:24]([C@H:21]3[CH2:20][CH2:19][C@H:18]([C@H:15]4[CH2:16][CH2:17][C@H:12]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH2:13][CH2:14]4)[CH2:23][CH2:22]3)=[O:26])[CH2:38][CH2:37]2)=[CH:34][CH:35]=1)[CH2:28][CH3:29]

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 65578Oxalyl chlorideHCID 178439125HCID 178439125, VerbindungHCID 178444515HCID 178444515, Verbindung

Produkt 1

HCID 178444516HCID 178444516, VerbindungAusbeute 44,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1049PyridineLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6342AcetonitrileLösungsmittel2×

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

A solution of 0.902 ml of dimethylformamide in 20 ml of acetonitrile was placed at -20° C. while gassing with argon in a sulphonation flask fitted with a mechanical stirrer, serum cap, thermometer and dropping funnel and treated within 2 minutes with 0.338 ml of oxalyl chloride. After completion of the addition, the mixture was stirred at -20° C. for a further 20 minutes and then 1.0 g of trans-4-(trans-4-pentylcyclohexyl)cyclohexanecarboxylic acid was introduced into the resulting white suspension via a solid substance addition tube. The mixture was subsequently stirred at -20° C. for 30 minutes and then treated dropwise at -20° C. within 10 minutes with a solution of 1.97 g of trans-4-(p-propylphenyl)cyclohexanol and 0.9 ml of pyridine in 20 ml of acetonitrile. The mixture was stirred for a further 15 hours while slowly warming to room temperature, then poured into 200 ml of cold 2N sodium carbonate solution and extracted three times with 200 ml of methylene chloride each time. The organic phases were washed once with 100 ml of 2N sodium carbonate solution and twice with 200 ml of water each time, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.5 bar) of the residue (2.6 g) on 140 g of silica gel using toluene/hexane (volume ratio 1:1) gave 757 mg (44%) of trans-4-(trans-4-pentylcyclohexyl)cyclohexanecarboxylic acid trans-4-(p-propylphenyl)cyclohexyl ester as colourless crystals. A single recrystallization from acetone yielded analytically-pure product of m.p. (C-S) 63.3° C., phase transition S-N 241.5° C., cl.p. (N-I) 285.5° C.

Aufarbeitung

  1. customwas placed at -20° C.
  2. customwhile gassing with argon in a sulphonation flask
  3. customfitted with a mechanical stirrer
  4. customserum cap
  5. additionAfter completion of the addition
  6. stirringThe mixture was subsequently stirred at -20° C. for 30 minutes
  7. stirringThe mixture was stirred for a further 15 hours
  8. temperaturewhile slowly warming to room temperature
  9. extractionextracted three times with 200 ml of methylene chloride each time
  10. washThe organic phases were washed once with 100 ml of 2N sodium carbonate solution and twice with 200 ml of water each time
  11. dry with materialdried over magnesium sulphate
  12. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-67a6f76002d14e738eb5bdcd9dffb553
Quelldatensatz
uspto-grants-1985_07
Patentnummer
US04526704

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