3-Bromophenol → 3-(3,7-Dimethyloctyloxy)bromobenzene

HRID 988936

Reaktionsgleichung

Reaktionsgleichung von HRID 988936
N[C@H](C(O)=O)CC1C=C2C(C=CC=C2)=CC=1.[OH-].[K+].[Br:19][C:20]1[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=1.[CH3:27][CH:28]([CH2:32][CH2:33][CH2:34][CH:35]([CH3:37])[CH3:36])[CH2:29][CH2:30]Cl>C(O)C>[CH3:27][CH:28]([CH2:32][CH2:33][CH2:34][CH:35]([CH3:37])[CH3:36])[CH2:29][CH2:30][O:26][C:22]1[CH:21]=[C:20]([Br:19])[CH:25]=[CH:24][CH:23]=1

Komponenten

6

Edukt 4

HCID 115633-BromophenolHCID 14797Potassium Hydroxide2×HCID 1859152-NaphthylalanineHCID 2273601-Chloro-3,7-dimethyloctane

Produkt 1

HCID 180041813-(3,7-Dimethyloctyloxy)bromobenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
32.5 °C

Versuchsvorschrift

450 ml of ethanol were initially introduced, and Nal (10.5 g; 70 mmol) and KOH (67.3 g; 1.2 mol) were added. A temperature increase from 25 to 40° C. after addition of the KOH was observed. After the mixture had been cooled to room temperate, 3-bromophenol (176.5 g; 1 mol) was added, during which the white suspension became beige. 3,7-Dimethyloctyl chloride (186.32 g; 212.94 ml; 1.05 mol) was added over the course of 3 minutes via a dropping funnel. The mixture was stirred at RT for a further 2 hours and subsequently stirred at an internal temperature of 80° C. for 96 hours. Ethanol was distilled off. The residue was taken up in ethyl acetate, and the precipitate was separated off by filtration. The organic phase was extracted three times with 10% strength by weight aqueous NaOH solution and washed once with H2O, three times with H2O which had been acidified using CO2 and again with H2O. After the mixture had been dried using MgSO4, the solvent was stripped off again in a rotary evaporator, and the crude product was purified by fractional distillation under reduced pressure.

Aufarbeitung

  1. additionwas added, during which the white suspension
  2. stirringsubsequently stirred at an internal temperature of 80° C. for 96 hours
  3. distillationEthanol was distilled off
  4. customthe precipitate was separated off by filtration
  5. extractionThe organic phase was extracted three times with 10% strength by weight aqueous NaOH solution
  6. washwashed once with H2O, three times with H2O which
  7. customAfter the mixture had been dried
  8. customthe solvent was stripped off again in a rotary evaporator
  9. distillationthe crude product was purified by fractional distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7b4334bc727e4fd09c7d8cae82bd40f8
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06638646B2

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