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

HRID 1089256

Reaction equation

HRID 1089256 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 2723924Mercury bis(trifluoroacetate)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-877aa27bbb244298bdf0934a84ff7f98
Source dataset
uspto-grants-1990_10
Patent number
US04965270

Linked notes

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