Butylated Hydroxyanisole → HCID 86668285, Verbindung

HRID 571575

Reaktionsgleichung

Reaktionsgleichung von HRID 571575
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]([CH3:13])([CH3:12])[CH3:11].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23].C(=O)(O)[O-].[Na+]>C(=O)(OC)OC>[CH3:21][S:22]([O:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]([CH3:13])([CH3:12])[CH3:11])(=[O:24])=[O:23]

Komponenten

6

Edukt 4

HCID 8456Butylated HydroxyanisoleHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium Bicarbonate

Produkt 1

HCID 86668285HCID 86668285, VerbindungAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 12021Dimethyl CarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

15.0 g (83.2 mmol) of 4-hydroxy-3-tert-butylanisole and 10.5 g (104 mmol) of triethylamine were dissolved in 250 ml of dimethyl carbonate (solvent), and 11.9 g (104 mmol) of methanesulfonyl chloride was dropwise added thereto, taking 25 minutes and controlling the inner temperature at 5° C. or lower. After the addition, this was stirred at 25° C. for 1.5 hours, the reaction mixture was poured into an aqueous saturated sodium bicarbonate solution, the aqueous layer was separated, the organic layer was washed twice with water, and then the organic layer was separated and concentrated. The concentrate was purified through distillation (139° C./32 pa) to give 16.3 g of 2-tert-butyl-4-methoxyphenyl methanesulfonate (yield, 76%).

Aufarbeitung

  1. customat 5° C.
  2. additionAfter the addition
  3. customthe aqueous layer was separated
  4. washthe organic layer was washed twice with water
  5. customthe organic layer was separated
  6. concentrationconcentrated
  7. distillationThe concentrate was purified through distillation (139° C./32 pa)

Quellen und Nachweise

ORD-Eintrag
ord-e6cb5f084f1e46d0a94f4f047535c050
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029024B2

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