Sodium borohydride → [1-(Benzyloxy)-2-naphthyl]methanol

HRID 433149Notes

Reaction equation

HRID 433149 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[CH:19]=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[CH2:19][OH:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 156178221-(Benzyloxy)-2-naphthaldehyde

Product 1

HCID 23431826[1-(Benzyloxy)-2-naphthyl]methanolYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(benzyloxy)-2-naphthaldehyde (7.00 g, 26.7 mmol) in methanol (250 mL) at 0° C. was added sodium borohydride (1.51 g, 40.0 mmol) and the reaction mixture was allowed to stir at room temperature for 24 h. The solvent was removed in vacuo to give a crude solid which was partitioned between ethyl acetate (300 mL) and water (300 mL). The organic layer was separated and washed with water (300 mL), aqueous sodium chloride (300 mL), dried (magnesium sulfate) and filtered through a plug of silica (10 cm×5 cm). The solvent was removed in vacuo to give 6.98 g (99%) of [1-(benzyloxy)-2-naphthyl]methanol as white crystalline solid. Rf=0.36 (silica, dichloromethane:hexanes 3:2); mp 85-87° C. Anal. Calcd. for C18H16O2: C, 81.24; H, 6.14. Found: C, 81.03; H, 5.98.

Workup

  1. customThe solvent was removed in vacuo
  2. customto give a crude solid which
  3. customwas partitioned between ethyl acetate (300 mL) and water (300 mL)
  4. customThe organic layer was separated
  5. washwashed with water (300 mL), aqueous sodium chloride (300 mL)
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered through a plug of silica (10 cm×5 cm)
  8. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d61f9339ea9642b3b576f5eac92c9754
Source dataset
uspto-grants-2003_12
Patent number
US06667322B2

Reaction notes

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