4-tert-Butyl-3-methoxybenzoic acid → 1206775-43-0

HRID 1517528Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1517528
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][C:6]=1[O:14][CH3:15])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:1]([C:5]1[CH:13]=[CH:12][C:8]([CH2:9][OH:10])=[CH:7][C:6]=1[O:14][CH3:15])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 127397584-tert-Butyl-3-methoxybenzoic acidHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 534014571206775-43-0Ausbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Preparation of 26—To a solution of 4-tert-butyl-3-methoxy-benzoic acid (3 g, 14.4 mmol, CASRN 79822-46-1) and THF (60 mL) cooled to 0° C. was added a solution of LiAlH4 in THF (29 mL, 28.8 mmol, 1M THF solution). The reaction was stirred overnight at RT then quenched by dropwise addition of aqueous THF (1.1 mL of water in 10 mL of THF) followed by 1.1 mL of 15% NaOH and then 3.3 mL of water. The reaction was stirred for 1 h then solid Na2SO4 was added and the resulting suspension stirred overnight, filtered through a pad of CELITE, and evaporated to afford 2.8 g of 4-tert-butyl-3-methoxy-benzyl alcohol.

Aufarbeitung

  1. customthen quenched by dropwise addition of aqueous THF (1.1 mL of water in 10 mL of THF)
  2. stirringThe reaction was stirred for 1 h
  3. additionsolid Na2SO4 was added
  4. stirringthe resulting suspension stirred overnight
  5. filtrationfiltered through a pad of CELITE
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-b7106af81a554c499723c24c022eb1be
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232271B2

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