Dichloromethane → Dichloromethane methanol ammonium hydroxide

HRID 1695307Notes

Reaction equation

HRID 1695307 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]([CH2:18][OH:19])[CH:13]=[C:14]([CH2:16][OH:17])[CH:15]=2)C(=O)C2=CC=CC=C12.O.NN.[Cl:29][CH2:30][Cl:31]>C(O)C>[OH-:9].[NH4+:5].[CH3:8][OH:9].[Cl:29][CH2:30][Cl:31].[NH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH2:18][OH:19])[CH:13]=[C:14]([CH2:16][OH:17])[CH:15]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 24654Hydrazine hydrate (1:1)HCID 57570851HCID 57570851, compound

Product 2

HCID 21896990Dichloromethane methanol ammonium hydroxideHCID 57570932HCID 57570932, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-(3-Phthalimido-propyloxy)-1,3-bis-(hydroxymethyl)-benzene (1.45 g) was dissolved in a mixture of dichloromethane and ethanol (25 mL, 25:75). Hydrazine hydrate (0.62 mL) was added and the reaction mixture was refluxed for 1 h. The solvent was removed in vacuo and the residue dissolved in dichloromethane. The insoluble residue was filtered off and purified by silica gel chromatography (Merck SuperVarioPrep 70 g column, Si60 15-40 μm), eluted with methanol/dichloromethane, 20:80 then ammonium hydroxide/methanol/dichloromethane, 0.5:25:75 to give 1-(3-amino-propyloxy)-3,5-bis-(hydroxy-methyl)-benzene (1 g) suitable for further transformation.

Workup

  1. temperaturethe reaction mixture was refluxed for 1 h
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue dissolved in dichloromethane
  4. filtrationThe insoluble residue was filtered off
  5. custompurified by silica gel chromatography (Merck SuperVarioPrep 70 g column, Si60 15-40 μm)
  6. washeluted with methanol/dichloromethane, 20:80

Sources & evidence

ORD record
ord-ea72d0e9ef164f8d993fa7becaa01e9b
Source dataset
uspto-grants-2012_04
Patent number
US08163736B2

Reaction notes

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