Sodium Hydroxide → HCID 18624180, compound

HRID 1860636Notes

Reaction equation

HRID 1860636 reaction equation
[OH-:1].[Na+].[CH2:3]([O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15]Cl)=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].C1C=CC=CC=1.O>[CH2:3]([O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][C:4]([CH3:9])([CH3:5])[CH:3]=[O:1])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 700424-Benzyloxybenzyl chloride

Product 1

HCID 18624180HCID 18624180, compoundYield 99.1%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 241BenzeneSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

A mixture of NaOH (0.7 g), and (Bu)4NI (0.15 g) in benzene (2.0 mL) and water (0.7 mL) was heated at 70° C. under argon to obtain a homogeneous mixture. To this mixture was added dropwise a mixture of isobutylaldehyde (1.44 g, Aldrich), and 4-benzyloxybenzyl chloride (3.5 g, Aldrich) in benzene (5.0 mL). After the addition, the resulting mixture was stirred at 70° C. for 3 h under argon. It was cooled, diluted with water, and extracted with EtOAc (3×25 mL). The combined organic extracts were washed with water, dried (anhydrous Na2SO4) and concentrated to dryness. This residue was purified by silica gel flash chromatography using 5% EtOAC in hexane. The appropriate fractions (monitored by TLC and ES mass spectrometry) were combined and concentrated to dryness to give the desired product (2.0 g, ˜50%) as a white powder: Rf=0.28 (10% EtOAc/Hexane), 1H -NMR (CDCl3) δ9.56 (s, 1H), 7.4 (m, 5H), 6.99 (d, 2H), 6.83 (d, 2H), 5.02 (s, 2H), 2.71 (s, 2H), 1.02 (6H); ES-MS m/z 286 (M+18); HRMS calcd C18H20O20NH4 (M+NH4) 286.2100, found 286.1833.

Workup

  1. customto obtain a homogeneous mixture
  2. additionTo this mixture was added dropwise
  3. additionAfter the addition
  4. temperatureIt was cooled
  5. extractionextracted with EtOAc (3×25 mL)
  6. washThe combined organic extracts were washed with water
  7. dry with materialdried (anhydrous Na2SO4)
  8. concentrationconcentrated to dryness
  9. customThis residue was purified by silica gel flash chromatography
  10. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-a42320f81a674a15a3082ea7786c0a9d
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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