2-(Benzyloxy)-5-bromobenzaldehyde → (2-(Benzyloxy)-5-bromophenyl)methanol

HRID 427749

Reaktionsgleichung

Reaktionsgleichung von HRID 427749
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:10]=1[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:10]=1[CH2:11][OH:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 7330872-(Benzyloxy)-5-bromobenzaldehydeHCID 4311764Sodium borohydride

Produkt 1

HCID 897136(2-(Benzyloxy)-5-bromophenyl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A suspension of 2-benzyloxy-5-bromobenzaldehyde (14.5 g, 50.2 mmol) in absolute ethanol (250 ml) was treated with sodium borohydride (2.6 g, 68.8 mmol). The reaction was stirred and the temperature slowly rose to 33° C. After 1 hour the reaction mixture was evaporated and the residue dissolved in ethyl acetate and poured into a mixture of ice water (200 ml) and 1N HCl (25 ml). The organic layer was separated, washed with aqueous sodium hydrogen carbonate, brine, dried (Na2SO4) and evaporated to give 2-benzyloxy-5-bromobenzyl alcohol as a pale yellow oil (14.85 g, quantitative).

Aufarbeitung

  1. customslowly rose to 33° C
  2. customAfter 1 hour the reaction mixture was evaporated
  3. dissolutionthe residue dissolved in ethyl acetate
  4. additionpoured into a mixture of ice water (200 ml) and 1N HCl (25 ml)
  5. customThe organic layer was separated
  6. washwashed with aqueous sodium hydrogen carbonate, brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-325e740b45744e5babf8867b57e39f40
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313148B1

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