Benzene → Hydroxymethyl-2-methyl-2-undecyl-1,3-dioxolane

HRID 2039438Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2039438
[CH3:1][C:2](=[O:14])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[OH:15][CH2:16][CH:17]([CH2:19][OH:20])O.C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[OH:15][CH2:16][CH:17]1[CH2:19][O:20][C:2]([CH3:1])([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[O:14]1

Komponenten

6

Edukt 4

HCID 241BenzeneHCID 753GlycerolHCID 6101p-Toluenesulfonic acidHCID 116222-Tridecanone

Produkt 1

HCID 10265274Hydroxymethyl-2-methyl-2-undecyl-1,3-dioxolane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Firstly, 100 g (0.5 mol) of 2-tridecanone (Aldrich P/N 17,283-9), 56 g (0.6 mol) of glycerol (Aldrich P/N 32,00-5), 200 mL of benzene, and 1.8 grams of p-toluenesulfonic acid (Aldrich P/N 40,2885) were placed in a 500 mL round bottom flask fitted with a Dean Stark apparatus. The mixture was heated to reflux with stirring until no further separation of water appeared. The reaction mixture was cooled to room temperature and washed successively with a 100 mL portion of 5% sodium carbonate solution and three 100 mL portions of water. The organic layer was dried over sodium sulfate, filtered and the benzene was removed with a rotary evaporator. The residual oil was fractionated by distillation under reduced pressure to give the desired product (b.p. 140° C./0.3 mm Hg). The identity of the product was confirmed by 1H NMR in CDCl3.

Aufarbeitung

  1. customfitted with a Dean Stark apparatus
  2. temperatureThe mixture was heated
  3. temperatureto reflux
  4. washwashed successively with a 100 mL portion of 5% sodium carbonate solution and three 100 mL portions of water
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. customthe benzene was removed with a rotary evaporator
  8. distillationThe residual oil was fractionated by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a3d622ee97a043e0b89090061f8f65c6
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08580533B2

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