Hydrochloric Acid → 2,4-Bis(benzyloxy)-5-isopropenylbenzoic acid

HRID 334889Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 334889
C([O:8][C:9](=[O:35])[C:10]1[CH:15]=[C:14]([C:16]([CH3:18])=[CH2:17])[C:13]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:12][C:11]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)C1C=CC=CC=1.[OH-].[Li+].Cl>C1COCC1.CO.O.O>[CH2:28]([O:27][C:11]1[CH:12]=[C:13]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:14]([C:16]([CH3:18])=[CH2:17])=[CH:15][C:10]=1[C:9]([OH:35])=[O:8])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 592631182,4-Bis-benzyloxy-5-isopropenyl-benzoic acid benzyl ester

Produkt 1

HCID 498640162,4-Bis(benzyloxy)-5-isopropenylbenzoic acidAusbeute 81,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 21892291Methanol tetrahydrofuran waterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 2,4-bis-benzyloxy-5-isopropenyl-benzoic acid benzyl ester (40.8 g, 87.9 mmol) in THF-MeOH-water (3:1:1, 300 mL total) was added lithium hydroxide (8.42 g, 352 mmol). The mixture was heated at 50° C. for 16 h, allowed to cool to ambient and then diluted with water (300 mL). The mixture was taken to pH˜1 using conc. HCl (˜30 mL) and then extracted with EtOAc (2×200 mL). The combined organic extracts were washed with brine, dried (MgSO4), filtered and reduced in vacuo. The solid residue was taken up in P.E-MeOH (9:1, 300 mL total), the slurry stirred for 1 h at ambient and the solid collected by filtration. The solid was dried in vacuo to give the title compound (26.8 g) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) 12.30 (s, 1H), 7.61 (s, 1H), 7.53 (d, J=7.0 Hz, 2H), 7.47-7.31 (m, 8H), 6.94 (s, 1H), 5.23 (d, J=14.0 Hz, 4H), 5.08 (d, J=9.0 Hz, 2H), 2.04 (s, 3H).

Aufarbeitung

  1. temperatureto cool to ambient and
  2. extractionextracted with EtOAc (2×200 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. filtrationcollected by filtration
  7. customThe solid was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e2c926a29d8e4b4893d73acf366ba4d0
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883790B2

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