Sodium Bicarbonate → (6-Bromonaphthalen-2-yl)methanol

HRID 446209Notes

Reaction equation

HRID 446209 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12](OC)=[O:13])[CH:6]=[CH:5]2.[H-].C([Al+]CC(C)C)C(C)C.C(=O)(O)[O-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH2:12][OH:13])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 8541342-Bromo-6-methoxycarbonylnaphthaleneHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 13473070(6-Bromonaphthalen-2-yl)methanolYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 6-bromo-2-naphthoate (5 g, 18.9 mmol) was dissolved in purified THF (100 mL) under a nitrogen atmosphere, the reaction solution was cooled down to 0° C., and then diisobutyl aluminum hydride (18.9 mL, 1.0M hexane solution) was added thereto. The reaction mixture solution was stirred at room temperature for 3 hours. Sodium bicarbonate (20 mL) was added to the reaction mixture solution, and then the solvent was removed by extraction with water and dichloromethane. The extracted material was dried in vacuum to thereby obtain a white solid (4.3 g, yield: 95%).

Workup

  1. customthe solvent was removed by extraction with water and dichloromethane
  2. customThe extracted material was dried in vacuum

Sources & evidence

ORD record
ord-b1571d08fcfd4e0289b13b9841a2c7e7
Source dataset
uspto-grants-2013_07
Patent number
US08476474B2

Reaction notes

Loading…