Hydrochloric Acid → Methyl 3-hydroxy-3-isopropyl-7-phenylheptanoic acid

HRID 1107145Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1107145
[OH:1][C:2]([CH:18]([CH3:20])[CH3:19])([CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:3][C:4]([O:6]C)=[O:5].[CH3:21]O.Cl>O>[CH3:21][CH:3]([C:2]([OH:1])([CH:18]([CH3:20])[CH3:19])[CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:4]([OH:6])=[O:5]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 18790185Methyl 3-hydroxy-3-isopropyl-7-phenylheptanoate

Produkt 1

HCID 18790083Methyl 3-hydroxy-3-isopropyl-7-phenylheptanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of 0.88 g (3.17 mmol) of the methyl 3-hydroxy-3-isopropyl-7-phenylheptanoate in 30 mL of 1:1:1-THF:MeOH:H2O is added 1.08 g (25.36 mmol, 8 eq) of LiOH monohydrate and this is stirred at 25° C. for 1 month. This mixture is then acidified to pH=6 with 1 N HCl and then partitioned between ethyl acetate and water. The organics are dried (Na2SO4) and concentrated in vacuo to afford methyl 3-hydroxy-3-isopropyl-7-phenylheptanoic acid in the form of a pale yellow crystalline solid. (0.59 g, 70%): 1H-NMR (300 MHz, CDCl3) δ (TMS) 0.98(d, 6H), 1.35(m, 1H), 1.55(m, 5H), 2.1(m, 1H), 2.35(t, 1H), 2.6(t, 2H), 3.88(m, 1H), 6.08(bs, 2H), 7.15(m, 3H), 7.25(m, 2H).

Aufarbeitung

  1. custompartitioned between ethyl acetate and water
  2. dry with materialThe organics are dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f6c69e02109e49e3ae604755daf56afa
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06057369

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