Dichloromethane → Benzeneethanol, 4-octyl-, 1-methanesulfonate

HRID 1505020Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1505020
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][OH:17])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].ClCCl.C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>O>[CH3:28][S:29]([O:17][CH2:16][CH2:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:14][CH:13]=1)(=[O:31])=[O:30]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 113108762-(4-Octylphenyl)ethanol

Produkt 1

HCID 21849441Benzeneethanol, 4-octyl-, 1-methanesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-(4-Octylphenyl)ethanol (53 g) and dichloromethane (500 mL) are charged into a 1 liter three-neck round bottom flask equipped with guard tube and addition funnel. Triethylamine (83.5 g) is added, the mixture is stirred for 30 minutes, then it is cooled to 0° C. Methanesulphonyl chloride (35.2 mL) is added drop-wise at 0° C. and the mass is stirred for 3 hours at room temperature. The mass is diluted with water (700 mL) and the organic layer is separated and the aqueous layer is extracted with dichloromethane (2×250 mL). The combined organic layers is washed with saturated sodium bicarbonate (500 mL) and brine solution (500 mL). The organic layer is separated, dried with sodium sulphate, and concentrated under vacuum to obtain the title compound. Yield: 70 g.

Aufarbeitung

  1. customequipped with guard tube and addition funnel
  2. stirringthe mass is stirred for 3 hours at room temperature
  3. customthe organic layer is separated
  4. extractionthe aqueous layer is extracted with dichloromethane (2×250 mL)
  5. washThe combined organic layers is washed with saturated sodium bicarbonate (500 mL) and brine solution (500 mL)
  6. customThe organic layer is separated
  7. dry with materialdried with sodium sulphate
  8. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1a1b93bd92454003970afd1ad09040cf
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216943B2

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