Sodium Chloride → 1,4-Bis(4-methoxybenzyloxy)butan-2-ol

HRID 1089256

Reaktionsgleichung

Reaktionsgleichung von HRID 1089256
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][O:8][CH2:9][CH:10]=[CH:11][CH2:12][O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[CH:5][CH:4]=1.[OH-:25].[Na+].[BH4-].[Na+].[Cl-].[Na+]>O1CCCC1.FC(F)(F)C([O-])=O.[Hg+2].FC(F)(F)C([O-])=O>[CH3:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][O:13][CH2:12][CH:11]([OH:25])[CH2:10][CH2:9][O:8][CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:24][CH:23]=2)=[CH:20][CH:19]=1

Komponenten

7

Edukt 4

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 545551371,4-Bis(4-methoxybenzyloxy)but-2-ene

Produkt 1

HCID 148142131,4-Bis(4-methoxybenzyloxy)butan-2-olAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2723924Mercury bis(trifluoroacetate)KatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of mercury (II) trifluoroacetate (17.1 g, 40 ml) in aqueous tetrahydrofuran (1:1, 80 ml) was added a solution of 1,4-bis(4-methoxybenzyloxy)but-2-ene (12.8 g, 39 mmol) in tetrahydrofuran (10 ml) over 5 minutes. The resulting 2-phase mixture was stirred vigorously at room temperature for 15 minutes. To the mixture was added aqueous sodium hydroxide (40 ml, 3M) followed by sodium borohydride (0.5M solution in 3M sodium hydroxide; 40 ml) with water-bath cooling. The solution was saturated with sodium chloride and allowed to stand. The organic layer was collected, dried (magnesium sulphate) and filtered through celite. The solvent was removed to afford 1,4-bis(4-methoxybenzyloxy)butan-2-ol (12.27 g, 91%), IR: υmax (KBr) 3440, 2940, 2860, 1610, 1510 and 1250 cm-1 ; 1H NMR: δH (CDCl3) 1.76 (2H, q, J=6.0 Hz, 3-H), 2.90 (1H, br, D2O exchangeable, OH), 3.41 (2H, AB of ABX JAX =6.9 Hz, JBX =4.2 Hz and JAB =9.5 Hz, 1-H), 3.62 (2H, m, 4-H), 3.80 (6H, s, 2×CH3), 4.00 (1H, m, 2-H), 4.43 (2H, s, ArCH2), 4.48 (2H, s, ArCH2), 6.86 (4H, m, ArH) and 7.24 (4H, m, ArH).

Aufarbeitung

  1. temperaturecooling
  2. customThe organic layer was collected
  3. dry with materialdried (magnesium sulphate)
  4. filtrationfiltered through celite
  5. customThe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-877aa27bbb244298bdf0934a84ff7f98
Quelldatensatz
uspto-grants-1990_10
Patentnummer
US04965270

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