Ethylene Glycol → HCID 19701587, Verbindung

HRID 1844228Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1844228
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[OH:11][CH2:12][CH2:13]O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]2[O:11][CH2:12][CH2:13][O:6]2)[CH:7]=[CH:8][C:9]=1[OH:10]

Komponenten

5

Edukt 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 763083-Bromo-4-hydroxybenzaldehyde

Produkt 1

HCID 19701587HCID 19701587, VerbindungAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

3-Bromo-4-hydroxybenzaldehyde (2a, 10.0 g, 49.8 mmol) was heated at reflux with 1,2-dihydroxyethane (25 g, 0.4 mol) in toluene (150 mL) in the presence of p-toluenesulfonic acid (950 mg) for 48 h in an apparatus fitted with a Dean-Stark trap. The reaction mixture was concentrated by reduced pressure evaporation, washed with aqueous sodium hydrogen carbonate, water, brine, dried over Na2SO4, evaporated to dryness and then passed through a short silica gel column using a hexanes-ethyl acetate mixture (5:1) with a few drops of triethylamine as eluent to afford the protected product 3a (11.0 g, 95%) as a crystalline solid. Rf=0.38 (25% EtOAc-hexanes): mp 76-78° C. IR (neat) 3351, 2954, 2891, 1608, 1499, 1431, 1284, 1100 cm−1; 1H NMR (300 MHz, CDCl3) δ 7.57 (d, J=1.8 Hz, 1H), 7.28 (dd, J=8.4, 2.4 Hz, 1H), 6.96 (d, J=8.7 Hz, 1H), 5.69 (s, 1H), 4.03 (m, 4H); 13C NMR (75 MHz, CDCl3) δ 152.9, 131.5, 130.2, 127.5, 115.8, 110.0, 102.7, 65.2; CIMS (m/z, rel intensity) 247 (MH++2, 7), 245 (MH+, 7), 203 (100), 201 (100), 175 (4), 173(5), 94 (1).

Aufarbeitung

  1. customfitted with a Dean-Stark trap
  2. concentrationThe reaction mixture was concentrated by reduced pressure evaporation
  3. washwashed with aqueous sodium hydrogen carbonate, water, brine
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-b63c841473d441b280d7a82029c69b0c
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946287B2

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