Potassium Hydroxide → 1-Hydroxymethyl-7-Methoxynaphthalene

HRID 1370767Notes

Reaction equation

HRID 1370767 reaction equation
C([O:4][CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH3:17])[CH:14]=2)[CH:9]=[CH:8][CH:7]=1)(=O)C.[OH-].[K+]>CO.O>[CH3:17][O:16][C:13]1[CH:14]=[C:15]2[C:10]([CH:9]=[CH:8][CH:7]=[C:6]2[CH2:5][OH:4])=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 185132061-Acetoxymethyl-7-methoxynaphthalene

Product 1

HCID 154530791-Hydroxymethyl-7-Methoxynaphthalene

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

34.5 g (0.15 mol) of the compound obtained in Step A are dissolved in 300 ml of methanol. 35 g (4 eq) of potassium hydroxide dissolved in 35 ml of water are added with vigorous stirring. After 3 hours at room temperature, the reaction mixture is hydrolysed over a mixture of ice/concentrated hydrochloric acid. The creamy white precipitate which forms is filtered off, washed several times with ice-cold water and dried over P2O5 using a dessicator. The title alcohol is recrystallised from a mixture of CH2Cl2/cyclohexane to yield white needles.

Workup

  1. additionare added with vigorous stirring
  2. additionthe reaction mixture is hydrolysed over a mixture of ice/concentrated hydrochloric acid
  3. filtrationThe creamy white precipitate which forms is filtered off
  4. washwashed several times with ice-cold water
  5. dry with materialdried over P2O5 using a dessicator
  6. customThe title alcohol is recrystallised from a mixture of CH2Cl2/cyclohexane
  7. customto yield white needles

Sources & evidence

ORD record
ord-029cb000bdc8442e92e5896d1e60f42d
Source dataset
uspto-grants-2003_06
Patent number
US06583319B1

Reaction notes

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