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

HRID 254099
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 254099
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:16][S:17][CH2:18][C:19]([O:21]CC)=[O:20])[O:13][CH2:12][C:11]([CH3:15])([CH3:14])[CH2:10][O:9]2)=[CH:4][CH:3]=1.[Li+].[OH-]>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:16][S:17][CH2:18][C:19]([OH:21])=[O:20])[O:9][CH2:10][C:11]([CH3:15])([CH3:14])[CH2:12][O:13]2)=[CH:4][CH:3]=1
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Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 86619094Ethyl ({[2-(4-chlorophenyl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetate

Produkt 1

HCID 66843234({[2-(4-Chlorophenyl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetic acidAusbeute 96,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Ethyl ({[2-(4-chlorophenyl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetate (3.36 g, 9.36 mmol) was dissolved in THF (45 ml) and cooled to 0° C. LiOH (0.79 g, 18.8 mmol) in water (12 ml) was added and the mixture was stirred for 18 h at room temperature. The solvents were evaporated. The crude product was extracted between water and diethyl ether. The aqueous layer was acidified using 2M HCl to pH 6 and extracted twice with CH2Cl2. The combined CH2Cl2 layers were dried (Na2SO4) and concentrated under reduced pressure to afford 2.98 g (96%) of the title compound as an yellow oil. 1H-NMR (CDCl3, 300 MHz): δ 0.62 (s, 3H), 1.34 (s, 3H), 2.95 (s, 2H), 3.34 (s, 2H), 3.45 (s, 4H), 7.4 (m, 4H)

Aufarbeitung

  1. customThe solvents were evaporated
  2. extractionThe crude product was extracted between water and diethyl ether
  3. extractionextracted twice with CH2Cl2
  4. dry with materialThe combined CH2Cl2 layers were dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6a342756751c4f76ac2a7409eb507e0b
Quelldatensatz
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07871998B2

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