Hydrochloric Acid → (6-methoxynaphthalen-2-yl)methanol

HRID 594321Notes

Reaction equation

HRID 594321 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]=[O:14])[CH:7]=[CH:6]2.[BH4-].[Na+].Cl>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH2:13][OH:14])[CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 769916-Methoxy-2-naphthaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 10012701(6-methoxynaphthalen-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of commercially available 6-methoxy-2-naphthaldehyde (200 mg; 1.07 mmol) in MeOH (5 ml) was treated portionwise at rt with NaBH4 (50 mg; 1.31 mmol), and the resulting mixture was further stirred at rt, under nitrogen, for 1 h. 2 M aq. HCl was added, and the organic solvent was removed under reduced pressure. AcOEt and water were added, and the separated organic layer was dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure affording (6-methoxynaphthalen-2-yl)methanol as a colorless solid. LC-MS (conditions E): tR=0.55 min.; no ionisation.

Workup

  1. customthe organic solvent was removed under reduced pressure
  2. additionAcOEt and water were added
  3. dry with materialthe separated organic layer was dried over anh. MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-1be3265d43d042ee96a7d9f08bf7dd1a
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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