Allyl chloride → 5-Bromo-1,3-dimethyl-2-((prop-2-en-1-yl)oxy)benzene

HRID 1094295

Reaktionsgleichung

Reaktionsgleichung von HRID 1094295
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=1.[CH2:11](Cl)[CH:12]=[CH2:13]>[OH-].[Na+].C(O)(C)C>[CH2:13]([O:9][C:5]1[C:6]([CH3:8])=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[CH3:10])[CH:12]=[CH2:11]

Komponenten

5

Edukt 2

HCID 7850Allyl chlorideHCID 169194-Bromo-2,6-dimethylphenol

Produkt 1

HCID 6412705-Bromo-1,3-dimethyl-2-((prop-2-en-1-yl)oxy)benzeneAusbeute 97,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3776IsopropanolLösungsmittelHCID 14798Sodium HydroxideLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 4-bromo-2,6-dimethyl-phenol (20.1 g, 100 mmol) and allylchloride (32.7 g, 428 mmol) in 3 N aq. NaOH (100 mL) and isopropanol (250 mL) is stirred at 60° C. for 15 h before it is diluted with 1 N aq. NaOH (100 mL). The mixture is extracted with diethyl ether (300 mL, 150 mL) and the combined org. extracts are washed with 1 N aq. NaOH (2×100 mL), 1 M aq. NaH2PO4 (50 mL), dried over Na2SO4, filtered and concentrated to give 2-allyloxy-5-bromo-1,3-dimethyl-benzene (23.6 g) as a yellow oil, LC-MS: tR=1.08 min, [M+1]+=241.20.

Aufarbeitung

  1. extractionThe mixture is extracted with diethyl ether (300 mL, 150 mL)
  2. washextracts are washed with 1 N aq. NaOH (2×100 mL), 1 M aq. NaH2PO4 (50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-92e72d389eec4d21b830ceb4fcb42399
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08133910B2

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