Hydrochloric Acid → alpha-Methyl-3-nitrobenzenemethanol

HRID 236066

Reaktionsgleichung

Reaktionsgleichung von HRID 236066
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11](O)=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].B.CSC.Cl.C1C[O:22]CC1>CO>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]([OH:22])[CH3:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 158763-Nitrophenylacetic acidHCID 12423031(Dimethyl sulfide)trihydroboron

Produkt 1

HCID 223135alpha-Methyl-3-nitrobenzenemethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

40 g of 3-nitrophenylacetic acid was added to a solution of 26 ml of 10M borane-methyl sulfide in 200 ml of THF, and the mixture was stirred at 25° C. for 3 hr. The solution was then acidified with HCl in methanol, followed by evaporation of the solvent. The product 3-nitrophenylethanol (IV, A=H) was partitioned between diethyl ether (Et2O) and aqueous sodium carbonate, and the Et2O layer dried over sodium sulfate. Evaporation of the Et2O afforded 34.8 g of 3-nitrophenylethanol (IV, A=H) as an oil.

Aufarbeitung

  1. customfollowed by evaporation of the solvent
  2. customThe product 3-nitrophenylethanol (IV, A=H) was partitioned between diethyl ether (Et2O) and aqueous sodium carbonate
  3. dry with materialthe Et2O layer dried over sodium sulfate
  4. customEvaporation of the Et2O

Quellen und Nachweise

ORD-Eintrag
ord-091978e79fea444b8caf8f27f8199d7c
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04642378

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