Potassium Hydroxide → (1-Bromonaphthalen-2-yl)methanol

HRID 330519Notes

Reaction equation

HRID 330519 reaction equation
[OH-].[K+].C([O:6][CH2:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]=1[Br:18])(=O)C>CO.O>[Br:18][C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[CH:17][C:8]=1[CH2:7][OH:6]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 131131991-Bromo-2-naphthalenemethanol acetate

Product 1

HCID 13113200(1-Bromonaphthalen-2-yl)methanolYield 96.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Potassium hydroxide (25.3 g, 0.45 mol) was added to a solution of 1-bromo-2-naphthalenemethanol acetate (105 g, 0.38 mol) in methanol (300 mL) at room temperature. The resulting yellow solution was stirred at room temperature for 3 hours, then diluted with water and a precipitate was formed. The mixture was extracted with ether (2×300 mL), and the combined organic layers were washed with water (250 mL), brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The pure product was obtained as a light yellow solid (86.8 g, 96%).

Workup

  1. customa precipitate was formed
  2. extractionThe mixture was extracted with ether (2×300 mL)
  3. washthe combined organic layers were washed with water (250 mL), brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4f26c98a44f848499412e17566def333
Source dataset
uspto-grants-1990_01
Patent number
US04897405

Reaction notes

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