1-Chloro-3,4-dihydronaphthalene-2-carboxaldehyde → (1-Chloro-3,4-dihydronaphthalen-2-yl)methanol

HRID 330268

Reaction equation

HRID 330268 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][C:5]=1[CH:14]=[O:15]>CO.C1COCC1>[Cl:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][C:5]=1[CH2:14][OH:15]

Participants

5

Reactant 2

HCID 767521-Chloro-3,4-dihydronaphthalene-2-carboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 14819335(1-Chloro-3,4-dihydronaphthalen-2-yl)methanolYield 102.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of sodium borohydride (2.83 g, 0.075 mol) in methanol (150 mL) at 0° C., was added dropwise a solution of 1-chloro-2-formyl-3,4-dihydronaphthalene (9.59 g, 0.05 mol) in dry THF (150 mL). The reaction was stirred at room temperature for 1 hour, carbon dioxide was cautiously bubbled through the reaction mixture for 15 minutes, and the resulting mixture was concentrated under reduced pressure. The residue was diluted with water (150 mL), extracted with ether (3×150 mL), dried (MgSO4) and concentrated to give 9.95 g (102%) of product as a yellow oil.

Workup

  1. customcarbon dioxide was cautiously bubbled through the reaction mixture for 15 minutes
  2. concentrationthe resulting mixture was concentrated under reduced pressure
  3. additionThe residue was diluted with water (150 mL)
  4. extractionextracted with ether (3×150 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a203c78374d04dca998de492e3dae3ff
Source dataset
uspto-grants-1990_01
Patent number
US04895860

Linked notes

Loading…