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

HRID 330268

Reaktionsgleichung

Reaktionsgleichung von HRID 330268
[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]

Komponenten

5

Edukt 2

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

Produkt 1

HCID 14819335(1-Chloro-3,4-dihydronaphthalen-2-yl)methanolAusbeute 102,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a203c78374d04dca998de492e3dae3ff
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04895860

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