Carbon Dioxide → 2-(4-(4-Chlorobutanoyl)phenyl)-2-methylpropanoic acid

HRID 413537

Reaktionsgleichung

Reaktionsgleichung von HRID 413537
[Mg].[C:2](=[O:4])=[O:3].Br[C:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:20])[CH2:16][CH2:17][CH2:18][Cl:19])=[CH:11][CH:10]=1)([CH3:8])[CH3:7].ClC(C1C=CC(C(=O)CCCCl)=CC=1)(C)C.Cl>[Br-].C([N+](CC)(CC)CC)C.[Ag].C(#N)C>[Cl:19][CH2:18][CH2:17][CH2:16][C:15]([C:12]1[CH:11]=[CH:10][C:9]([C:6]([CH3:8])([CH3:7])[C:2]([OH:4])=[O:3])=[CH:14][CH:13]=1)=[O:20]

Komponenten

9

Edukt 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 5462224MagnesiumHCID 100635791-Butanone, 1-[4-(1-bromo-1-methylethyl)phenyl]-4-chloro-HCID 234998621-[4-(1-Chloro-1-methyl-ethyl)-phenyl)-4-chloro-butan-1-one

Produkt 1

HCID 109235672-(4-(4-Chlorobutanoyl)phenyl)-2-methylpropanoic acidAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6285Tetraethylammonium BromideKatalysatorHCID 23954SilverKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Fit a jacketed glass cell of about 6L capacity with a rotating expanded silver mesh cathode/magnesium anote assembly, a carbon dioxide deliver tube, and a stainless steel thermocouple. Load the cell with acetonitrile (5.8L) and tetraethylammonium bromide (26 g). Sparge with carbon dioxide and cool in cooling bath. When the contents of the cell reach −10° C., add hydrogen chloride remediated 1-[4-(1-bromo-1-methyl-ethyl)-phenyl]-4-chloro-butan-1-one and 1-[4-(1-chloro-1-methyl-ethyl)-phenyl]-4-chloro-butan-1-one (424.9 g, 53.5 mole % bromo and 20.4 mole % chloro by HPLC analysis, 1087 mmol total active tertiary benzylic halide) and perform electrolysis at a controlled current of 8 amps (20 mA cm−2) for 6 hours. Drain the contents, acidify with chilled aqueous 6M hydrochloric acid, extract, evaporate the solvent in vacuo and recrystallize to give the title compound (186 g, 64%); 78.5-80.3° C.

Aufarbeitung

  1. customSparge with carbon dioxide
  2. temperaturecool
  3. temperaturein cooling bath
  4. customreach −10° C.
  5. additionadd hydrogen chloride
  6. customfor 6 hours
  7. extractionextract
  8. customevaporate the solvent in vacuo
  9. customrecrystallize

Quellen und Nachweise

ORD-Eintrag
ord-99d4d94f26454c879aa54042cc48c561
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06566526B2

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