Potassium Carbonate → HCID 57570851, compound

HRID 1695308Notes

Reaction equation

HRID 1695308 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([OH:11])[CH:6]=[C:7]([CH2:9][OH:10])[CH:8]=1.Br[CH2:13][CH2:14][CH2:15][N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:17]1(=[O:26])[N:16]([CH2:15][CH2:14][CH2:13][O:11][C:5]2[CH:4]=[C:3]([CH2:2][OH:1])[CH:8]=[C:7]([CH2:9][OH:10])[CH:6]=2)[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]12

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21611N-3-BromopropylphthalimideHCID 15194153,5-Di(hydroxymethyl)phenol

Product 1

HCID 57570851HCID 57570851, compoundYield 27.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3,5-Bis-hydroxymethylphenol (Felder, D.; Gutierrez Nava, M.; del Pilar Carreon, M.; Eckert, J. F.; Luccisano, M.; Schall, C.; Masson, P.; Gallani, J. L.; Heinrich, B.; Guillon, D.; Nierengarten, J. F. Helv. Chimica Acta 2002, 85, 288) (2.35 g), N-(3-bromo-propyl)-phthalimide (4.49 g) and potassium carbonate (10.53 g) were mixed in acetonitrile (25 mL) and refluxed for 12 h. The reaction mixture was cooled to room temperature and the solvent removed under reduced pressure. The residue was redissolved in dichloromethane and the insoluble residue filtered off. The filtrate was washed with water, dried over magnesium sulfate, and concentrated in vacuo to a residue. The residue was purified by silica gel chromatography (Merck SuperVarioPrep 90 g column, Si60 15-40 μm), eluted with methanol/dichloromethane, 4:96 to give 5-(3-phthalimido-propyloxy)-1,3-bis-(hydroxymethyl)benzene (1.45 g):

Workup

  1. temperaturerefluxed for 12 h
  2. customthe solvent removed under reduced pressure
  3. dissolutionThe residue was redissolved in dichloromethane
  4. filtrationthe insoluble residue filtered off
  5. washThe filtrate was washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo to a residue
  8. customThe residue was purified by silica gel chromatography (Merck SuperVarioPrep 90 g column, Si60 15-40 μm)
  9. washeluted with methanol/dichloromethane, 4:96

Sources & evidence

ORD record
ord-2f2bebf98ff64f6792c40966da0f8e0d
Source dataset
uspto-grants-2012_04
Patent number
US08163736B2

Reaction notes

Loading…