Formaldehyde → Butoxy-2-(2-hydroxyethyl)benzoic acid

HRID 1887537Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1887537
C(O[C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[C:8]([CH3:15])[CH:7]=1)CCC.[Li+].CC([N-]C(C)C)C.C(NC(C)C)(C)C.[CH2:31]([Li])[CH2:32][CH2:33][CH3:34].C=[O:37].C1[CH2:42][O:41]CC1>O>[CH2:31]([O:37][C:7]1[C:8]([CH2:15][CH2:42][OH:41])=[C:9]([CH:13]=[CH:14][CH:6]=1)[C:10]([OH:12])=[O:11])[CH2:32][CH2:33][CH3:34]

Komponenten

8

Edukt 6

HCID 712FormaldehydeHCID 7912DiisopropylamineHCID 8028Tetrahydrofuran2×HCID 2724682Lithium diisopropylamideHCID 534398994-Butoxy-2-methylbenzoic acidHCID 178418339Butyllithium

Produkt 1

HCID 68919863Butoxy-2-(2-hydroxyethyl)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 4-butoxy-2-methylbenzoic acid (2.5 g) in THF (15 mL) was added dropwise to a solution of LDA (freshly prepared from diisopropylamine (4.86 g) and n-butyllithium (32 mL; 1.5 M in hexane)) in THF (50 mL) at −78° C. After 10 minutes, paraformaldehyde (1.44 g) was added, and the mixture was allowed slowly to warm to room temperature. After 4 hours, water (10 mL) was added, and the volatile organic constituents were removed in a rotary evaporator. The residue was partitioned between water and diethyl ether. The aqueous phase was mixed with dichloromethane and cautiously acidified with hydrochloric acid at 0° C. Concentration of the organic phase afforded the desired product with the molecular weight of 238.29 (C13H18O4); MS (ESI): 239 (M+H+).

Aufarbeitung

  1. waitAfter 4 hours
  2. customthe volatile organic constituents were removed in a rotary evaporator
  3. customThe residue was partitioned between water and diethyl ether
  4. additionThe aqueous phase was mixed with dichloromethane
  5. customcautiously acidified with hydrochloric acid at 0° C

Quellen und Nachweise

ORD-Eintrag
ord-c0febd48cee94f539b441a0e35c5135d
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501771B2

Notizen zur Reaktion

Wird geladen…