Diethyl Ether → 6-(Hydroxymethyl)naphthalen-2-ol

HRID 48099

Reaction equation

HRID 48099 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[CH:14]=[C:13]([C:18](O)=[O:19])[CH:12]=[CH:11]2.C(OCC)C>C1COCC1>[OH:19][CH2:18][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([OH:7])[CH:17]=[CH:16]2

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 855576-Hydroxy-2-naphthoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 113327606-(Hydroxymethyl)naphthalen-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To the slurry of lithium aluminum hydride (2 equi.) in THF (3 mL/mmole), a solution of 6-hydroxy-naphthalene-2-carboxylic acid (15) (1 equi.) in THF (3 ml/mmole) was added at ice temperature over a period of 20 min. The reaction mixture was stirred at room temperature for 24 h, cooled to ice temperature, added diethyl ether (20 mL/mmole), quenched slowly with water (1 mL/g LAH), 15% aqueous sodium hydroxide (1 mL/g LAH), and water (3 mL/g LAH) succesively. MgSO4 (5 g/100 mL reaction solution) was added to the reaction mixture, stirred for 30 min, filtered through celite, and concentrated in vacuo to give 6-hydroxy methyl-naphthalen-2-ol (16), a white solid (79%).

Workup

  1. temperaturecooled to ice temperature
  2. customquenched slowly with water (1 mL/g LAH), 15% aqueous sodium hydroxide (1 mL/g LAH), and water (3 mL/g LAH) succesively
  3. additionMgSO4 (5 g/100 mL reaction solution) was added to the reaction mixture
  4. stirringstirred for 30 min
  5. filtrationfiltered through celite
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ebfc371689ab4c03a1c2c4bceff1b46c
Source dataset
uspto-grants-2004_03
Patent number
US06703082B1

Linked notes

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