Salicylic Acid → 2-(5-(Tetradecyloxy)furan-2-carbonyloxy)benzoic acid

HRID 335544

Reaktionsgleichung

Reaktionsgleichung von HRID 335544
[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([OH:23])=[O:22])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C(Cl)(=O)C(Cl)=O.[C:30]([OH:39])(=[O:38])[C:31]1[C:32](=[CH:34][CH:35]=[CH:36][CH:37]=1)O.CCN(CC)CC>C(Cl)Cl.CN(C)C=O.CCOC(C)=O>[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([O:23][C:37]2[CH:36]=[CH:35][CH:34]=[CH:32][C:31]=2[C:30]([OH:39])=[O:38])=[O:22])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Komponenten

8

Edukt 4

HCID 338Salicylic AcidHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 1151755-(Tetradecyloxy)-2-furoic acid

Produkt 1

HCID 498697632-(5-(Tetradecyloxy)furan-2-carbonyloxy)benzoic acidAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a cooled (0° C.) and stirred suspension of 5-(tetradecyloxy)furan-2-carboxylic acid (0.324 g, 1 mmol) in 10 mL of CH2Cl2 was added oxalyl chloride (0.135 mL, 1.5 mmol) and 2 drops of N,N-dimethylformamide. Immediate effervescence was observed. The solution was allowed to warm to room temperature with continued stirring until such a time that gas evolution had ceased and all suspended solids had dissolved. The solution was then cooled to 0° C. once more and salicylic acid (0.180 g, 1.3 mmol) and Et3N (3 mL) were added to the rapidly stirred reaction. After stirring for 2 hrs, the reaction was diluted with EtOAc (100 mL) and the organic phase was washed with 1M HCl (2×100 mL) and brine (100 mL) and then dried and concentrated to give a white solid residue. The crude material was purified by flash chromatography eluting with 5-40% EtOAc in Hexanes with 1% AcOH. The resulting material was further purified by recrystallization from CH2Cl2 and hexanes to yield 0.225 g (57%) of the title compound as a white crystalline material. 1H NMR (300 MHz, CDCl3) δ: 8.08 (dd, 1H), 7.62 (dt, 1H), 7.32-7.38 (m, 2H), 7.24 (dd, 1H), 5.39 (d, 1H), 4.18 (t, 2H), 1.80 (p, 2H), 1.2-1.5 (m, 22H), 0.88 (t, 3H).

Aufarbeitung

  1. temperatureto warm to room temperature
  2. stirringwith continued stirring until such a time that gas evolution
  3. dissolutionall suspended solids had dissolved
  4. temperatureThe solution was then cooled to 0° C. once more
  5. stirringAfter stirring for 2 hrs
  6. washthe organic phase was washed with 1M HCl (2×100 mL) and brine (100 mL)
  7. customdried
  8. concentrationconcentrated
  9. customto give a white solid residue
  10. customThe crude material was purified by flash chromatography
  11. washeluting with 5-40% EtOAc in Hexanes with 1% AcOH
  12. customThe resulting material was further purified by recrystallization from CH2Cl2 and hexanes

Quellen und Nachweise

ORD-Eintrag
ord-25fa2b5ee51e443b875068b53b0c19db
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08884034B2

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