Ammonium Chloride → HCID 54573647, compound

HRID 275175Notes

Reaction equation

HRID 275175 reaction equation
[CH2:1]([O:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:15]=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[BH4-].[Na+].[Cl-].[NH4+]>CO.C1COCC1>[CH2:1]([O:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:15][OH:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 27249293,4-didecoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 54573647HCID 54573647, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3,4-Didecyloxybenzaldehyde (6.78 g., 16.2 mmol, 1 equiv.) is dissolved in 44 mL of methanol and 20 mL of THF. Sodium borohydride (0.613 g., 16.2 mmol, 1 equiv.) is added in portions. The mixture is stirred for 30 minutes at room temperature. The solution is poured into saturated ammonium chloride solution, and then extracted twice with EtOAc. The organic extracts are washed with brine, dried (MgSO4), and evaporated. Chromatography on silica gel using 10%-20% EtOAc/hexane affords 3,4-didecyloxybenzyl alcohol (12a) (5.71 g., 13.6 mmol, 84%) as a clear oil: mp=41°-42.5° C.; UVmax (EtOH) 206 nm (ε=19085), 232 nm (ε=5340), 280 nm (ε=2239); 1H NMR (300 MHz, CDCl3) δ 6.90 (s, 1H, ArH), 6.83 (s, 1H, ArH), 6.83 (s, 1H, ArH), 4.58 (d, J=6 Hz, 2H, ArCH2OH), 3.96 (m, 4H, RCH2O), 1.79 (m, 4H, RCH2CH2O), 1.58 (t, J=6 Hz, 1H, OH), 1.44 (m, 4H, decyl), 1.25 (m, 24H, decyl), 0.86 (m, 6H, 2×CH3); 13C NMR (75 MHz, CDCl3) δ 149.34, 148.72, 133.68, 119.58, 113.83, 112.95, 69.42, 69.21, 65.41, 31.92, 29.64, 29.59, 29.43, 29.36, 29.30, 26.04, 22.69, 14.12; IR (KBr) 3346, 2956, 2922, 2850, 1520, 1468, 1262, 1236, 1138 m-1 ; MS (DCI) m/e 421 (MH+), 403 (M--OH). Anal. Calcd for C27H48O3 : C, 77.09; H, 11.50. Found: C, 77.26; H, 11.61.

Workup

  1. extractionextracted twice with EtOAc
  2. washThe organic extracts are washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-6dd25b5e0c3c468aa668cba10e4001fb
Source dataset
uspto-grants-1995_02
Patent number
US05391817

Reaction notes

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