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

HRID 47951Notes

Reaction equation

HRID 47951 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. is added sodium borohydride (1.51 g, 40.0 mmol) and the reaction mixture is allowed to stir at room temperature for 24 h. The solvent is removed in vacuo to give a crude solid which is partitioned between ethyl acetate (300 mL) and water (300 mL). The organic layer is 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 is 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 is removed in vacuo
  2. customto give a crude solid which
  3. customis partitioned between ethyl acetate (300 mL) and water (300 mL)
  4. customThe organic layer is 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 is removed in vacuo

Sources & evidence

ORD record
ord-0a0cfbe59340489193659de144a8f45d
Source dataset
uspto-grants-2004_03
Patent number
US06700001B2

Reaction notes

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