Lithium Hydroxide → ({[2-(4-Methoxyphenyl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetic acid

HRID 254087Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 254087
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH2:17][S:18][CH2:19][C:20]([O:22]CC)=[O:21])[O:14][CH2:13][C:12]([CH3:16])([CH3:15])[CH2:11][O:10]2)=[CH:5][CH:4]=1.[Li+].[OH-]>O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH2:17][S:18][CH2:19][C:20]([OH:22])=[O:21])[O:14][CH2:13][C:12]([CH3:16])([CH3:15])[CH2:11][O:10]2)=[CH:5][CH:4]=1

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 86619088Ethyl ({[2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetate

Produkt 1

HCID 66842966({[2-(4-Methoxyphenyl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetic acidAusbeute 98,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Ethyl ({[2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetate (5.95 g, 16.8 mmol) was dissolved in THP (75 ml) and cooled to 0° C. LiOH (2.11 g, 50.4 mmol) in water (40 ml) was added and the mixture was stirred for 90 minutes. Water was added and the mixture was extracted twice with diethyl ether. The aqueous layer was acidified using 2M HCl until pH=4 and extracted twice with CH2Cl2. The combined CH2Cl2 layers were dried (Na2SO4) and concentrated under reduced pressure to afford 5.4 g (>98%) of the title compound as a white solid. 1H-NMR (CDCl3, 200 MHz): δ 0.6 (s, 3H), 1.4 (s, 3H), 3.0 (s, 2H), 3.4 (s, 2H), 3.5 (s, 4H), 3.9 (s, 3H), 6.9 (d, 2H), 7.4 (d, 2H).

Aufarbeitung

  1. extractionthe mixture was extracted twice with diethyl ether
  2. extractionextracted twice with CH2Cl2
  3. dry with materialThe combined CH2Cl2 layers were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8909f83d352d401cbbb6872adefa3786
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07871998B2

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