Methanol → 2,6-Bis(hydroxymethyl)naphthalene

HRID 348731

Reaction equation

HRID 348731 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]2[CH:11]=[C:12]([C:15](OC)=[O:16])[CH:13]=[CH:14][C:7]=2[CH:6]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].CO.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1COCC1>[OH:2][CH2:3][C:5]1[CH:10]=[CH:9][C:8]2[C:7](=[CH:14][CH:13]=[C:12]([CH2:15][OH:16])[CH:11]=2)[CH:6]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 61225Dimethyl-2,6-naphthalenedicarboxylateHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydride

Product 1

HCID 117887222,6-Bis(hydroxymethyl)naphthaleneYield 101.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,6-naphthalene dicarboxylic acid dimethyl (5.00 g) was dissolved in anhydrous THF (150 ml) and added with lithium aluminum hydride (1.55 g) under ice-cooling, followed by stirring at room temperature for 2 hours under a nitrogen atmosphere. After completion of the reaction, methanol and an aqueous potassium sodium tartrate solution were added to the solution in this order and the whole was stirred overnight. The solution was subjected to extraction with chloroform and ethyl acetate and the extract was then washed with saturated saline solution. Subsequently, the organic layer was dried with anhydrous sodium sulfate and the solvent was distilled off, thereby obtaining the subject compound (3.90 g) as a white solid.

Workup

  1. temperaturecooling
  2. stirringthe whole was stirred overnight
  3. extractionThe solution was subjected to extraction with chloroform and ethyl acetate
  4. washthe extract was then washed with saturated saline solution
  5. dry with materialSubsequently, the organic layer was dried with anhydrous sodium sulfate
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-dd915030c75a480387658c51cf646155
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Linked notes

Loading…