Benzene → HCID 86651356, Verbindung

HRID 39497

Reaktionsgleichung

Reaktionsgleichung von HRID 39497
[Cl:1][CH:2]([CH2:6][OH:7])[C:3]([OH:5])=[O:4].[CH2:8](O)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[Cl:1][CH:2]([CH2:6][OH:7])[C:3]([O:5][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH3:8])=[O:4]

Komponenten

6

Edukt 4

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 81931-DodecanolHCID 5649512-Chloro-3-hydroxypropionic acid2×

Produkt 1

HCID 86651356HCID 86651356, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-chloro-3-hydroxypropionic acid (4.80 g, 0.03 mol), dodecanol (6.00 g, 0.03 mol) were taken with 5 mL dry benzene in a (50 mL) RB, with a dean-stark apparatus and condenser; 25 mg (0.26 mmol) para-Toluene sulfonic acid (pTSA) was added to it and the mixture was stirred at 75° C.-80° C. for 40 h. 1H-NMR showed 85% conversion. More 2-chloro-3-hydroxypropionic acid (1.00 g, 8.00 mmol) was added to it and heated at 75° C.-80° C. for 20 h. 1H-NMR showed almost complete conversion. After cooling it down, the product was added with 100 mL of CH2Cl2. Organic phase was washed twice with 50 mL of dil. NaHCO3 aq. sol. and once with 50 mL of sat. NaCl aq. sol. and then dried over anhy. Na2SO4. After filtration and removing the solvent by rotary evaporation, yield=7.76 g (78%). It was used for the next reaction without further purification. 1H-NMR (CDCl3, 7.27 ppm): 2.18-2.40 (broad, —OH), 3.97 (m, —CH2OH), 4.21 (m, —CO2CH2), 4.39 (m, —CHCl).

Aufarbeitung

  1. temperatureheated at 75° C.-80° C. for 20 h
  2. temperatureAfter cooling it down
  3. washOrganic phase was washed twice with 50 mL of dil. NaHCO3 aq. sol. and once with 50 mL of sat. NaCl aq. sol.
  4. customdried over anhy
  5. filtrationAfter filtration
  6. customremoving the solvent
  7. customby rotary evaporation, yield=7.76 g (78%)
  8. customIt was used for the next reaction without further purification

Quellen und Nachweise

ORD-Eintrag
ord-dd70758721d642d29d1cf230ba39a7bb
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524942B2

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