Water → Diphenylmethane

HRID 649233

Reaktionsgleichung

Reaktionsgleichung von HRID 649233
C([Li])CCC.C(C1N=CN([C:16](C2C=CC=CC=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)C=1)(=O)CCC.[Cl-].[NH4+].O>C1COCC1.CCCCCC>[C:17]1([CH2:16][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 147363744-Butanoyl-1-trityl-imidazoleHCID 178418339Butyllithium

Produkt 1

HCID 7580DiphenylmethaneAusbeute 200 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

A solution of 4.30 g (25.8 mmols) of diphenylmethane in 50 ml of THF is prepared in inert atmosphere (nitrogen) then cooled in an ice bath. First 16.7 ml of butyllithium of a 1.7M solution in hexane and then, drop by drop, a solution of 4.90 g (12.9 mmols) of the previous ketone 3 in 50 ml of THF, are added slowly. The resultant mixture is stirred for 2 hours at room temperature and then 50 ml of a saturated aqueous solution of ammonium chloride and 100 ml of water are added. Extraction with ethyl acetate followed by evaporation of the previously dried extracts yields alcohol 4 which is recrystallised in cyclohexane.

Aufarbeitung

  1. temperaturethen cooled in an ice bath
  2. extractionExtraction with ethyl acetate
  3. customfollowed by evaporation of the previously dried extracts

Quellen und Nachweise

ORD-Eintrag
ord-706d9badff444c799cbd39809ca4d99a
Quelldatensatz
uspto-grants-1988_04
Patentnummer
US04738979

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