Diethyl Ether → 2-Hydroxymethyl-5,6,7-trimethoxynaphthalene

HRID 720302Notes

Reaction equation

HRID 720302 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[C:18]([O:19][CH3:20])=[C:17]([O:21][CH3:22])[CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][C:13]([C:23](O)=[O:24])=[CH:14]2.CCOCC.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[OH:24][CH2:23][C:13]1[CH:12]=[CH:11][C:10]2[C:15](=[CH:16][C:17]([O:21][CH3:22])=[C:18]([O:19][CH3:20])[C:9]=2[O:8][CH3:7])[CH:14]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 62649Sodium sulfate decahydrateHCID 30179615,6,7-Trimethoxy-2-naphthoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 218915782-Hydroxymethyl-5,6,7-trimethoxynaphthalene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (579 mg) was added to dry THF (40 mL) under an argon atmosphere and ice cooling, a solution of 5,6,7-trimethoxynaphthalene-2-carboxylic acid (4.0 g) in dry THF (40 mL) was then added dropwise thereto, and the mixture was stirred at room temperature for 4 hours. Ether (150 mL) was added to the reaction mixture, sodium sulfate decahydrate was added thereto, and the resultant mixture was stirred for 15 minutes. The reaction mixture was filtered, the filtrate was concentrated, and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:2) to obtain the title compound.

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customthe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-9496f69053604f698aa27c6c6908ce65
Source dataset
uspto-grants-2006_11
Patent number
US07135473B2

Reaction notes

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