Sodium Hydroxide → Dodecanoic acid, 12-(triphenylmethoxy)-

HRID 467392

Reaktionsgleichung

Reaktionsgleichung von HRID 467392
C(OCCCCCCCCC(O)=O)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[OH-].[Na+].C[O:35][C:36](=[O:68])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][O:48][C:49]([C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1)([C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>C1COCC1>[C:49]([O:48][CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][C:36]([OH:68])=[O:35])([C:56]1[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=1)([C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1)[C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 426243679-Trityloxy-nonanoic acidHCID 67200799Methyl-12-trityloxy-dodecanoate

Produkt 1

HCID 10790077Dodecanoic acid, 12-(triphenylmethoxy)-Ausbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The synthesis and purification procedures of 16b were followed. Aqueous 0.5 M NaOH (4.6 mL, 2.3 mmol), 15c (548 mg, 1.2 mmol), and THF (9.3 mL) were used and the reaction duration was shortened to 2 days. After purification, 463 mg (87%) of 16c was obtained as a colorless oil. 1H-NMR (400 MHz, CDCl3, δH ppm): 7.43 (6H, m, p-Ar), 7.28 (6H, m, m-Ar), 7.21 (3H, m, o-Ar), 3.02 (2H, t, 3JH—H=6.7 Hz, HO—CH2), 2.34 (2H, t, 3JH—H=7.5 Hz, CH2CO2), 1.55-1.67 (4H, m, 2CH2), 1.19-1.39 (14H, m, 7CH2). 13C-NMR (100 MHz, CDCl3, δH ppm): 180.02, 144.53, 128.69, 127.64, 126.75, 86.25, 63.66, 34.02, 30.04, 29.52, 29.50, 29.48, 29.39, 29.22, 29.05, 26.25, 24.66. HRMS (EI): m/z calcd 458.2821 (C31H38O3), found 458.2814 [M]+.

Aufarbeitung

  1. customAfter purification

Quellen und Nachweise

ORD-Eintrag
ord-f1274027d74f4719b5ce8bf6a006978a
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623326B2

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