Hydrochloric Acid → 3,3,6-trimethylbenzo[c][1,2]oxaborol-1(3H)-ol

HRID 1037074Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1037074
C(OCOC([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=1[B:16]1[O:20][C:19]([CH3:22])([CH3:21])C(C)(C)[O:17]1)(C)C)C.Cl>C1COCC1>[CH3:22][C:19]1([CH3:21])[O:20][B:16]([OH:17])[C:10]2[CH:11]=[C:12]([CH3:15])[CH:13]=[CH:14][C:9]1=2

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 866855182-(2-(2-(Ethoxymethoxy)propan-2-yl)-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Produkt 1

HCID 866854553,3,6-trimethylbenzo[c][1,2]oxaborol-1(3H)-olAusbeute 51,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of compound 2-(2-(2-(ethoxymethoxy)propan-2-yl)-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (76.2 mmol) in THF (100 mL) was added 6 N HCl (381 mL). The reaction mixture was stirred at rt overnight, and the obtained mixture was extracted three times with ethyl acetate. The combined extracts were washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel eluted with PE-EA (20:1) to give 3,3,6-trimethylbenzo[c][1,2]oxaborol-1(3H)-ol (6.87 g; yield 51.2% over 2 steps) as a white solid. MS: m/z=177.1 (M+1, ESI+).

Aufarbeitung

  1. extractionthe obtained mixture was extracted three times with ethyl acetate
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography over silica gel
  7. washeluted with PE-EA (20:1)

Quellen und Nachweise

ORD-Eintrag
ord-9190e62866e146bdae46ed8e5d66f050
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546357B2

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