Water → HCID 178460514, Verbindung

HRID 726512

Reaktionsgleichung

Reaktionsgleichung von HRID 726512
[C:1]1([C@H:7]2[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:14]1C[CH2:17][CH2:16][CH2:15]1.C(N(CC)CC)C.O>C(Cl)(=O)C=C.C1C=CC=CC=1>[C:15]([O:13][C@H:10]1[CH2:9][CH2:8][C@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:12][CH2:11]1)(=[O:14])[CH:16]=[CH2:17]

Komponenten

7

Edukt 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 178521548HCID 178521548, Verbindung

Produkt 1

HCID 178460514HCID 178460514, VerbindungAusbeute 55,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 13140Acryloyl chlorideLösungsmittel

Versuchsvorschrift

First, 2.5 g of trans-4-phenylcyclohexanol, 50 ml of tetrahydrofuran, and 1.8 g of triethylamine were placed in a 100 ml flask. A solution in which 1.7 g of acryloyl chloride was dissolved in 5 ml of benzene was added dropwise to the mixture under ice water cooling. The mixture was allowed to warm to room temperature and stirred for 5 hours. Water was added to the reaction mixture, and an organic layer was extracted with ether. The ether layer was washed with water and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=10/1) and recrystallized from acetone to obtain 1.8 g of trans-4-phenylcyclohexyl acrylate (Y: 55.1%). The compound thus obtained had a purity of 99.7% by GC and 1 spot by TLC. Furthermore, the compound had an m.p. of 67.3° C.

Aufarbeitung

  1. additionwas added dropwise to the mixture under ice water cooling
  2. extractionan organic layer was extracted with ether
  3. washThe ether layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThereafter, the solvent was distilled away
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=10/1)
  7. customrecrystallized from acetone

Quellen und Nachweise

ORD-Eintrag
ord-2f59842550574b84b178087ad9bd6712
Quelldatensatz
uspto-grants-1998_01
Patentnummer
US05709911

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