Hydrochloric Acid → 3-[4-(2-Acetoxyethoxy)phenyl]-5,7-di-tert-butylbenzofuran-2-one

HRID 22496

Reaktionsgleichung

Reaktionsgleichung von HRID 22496
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[OH:16][CH2:17][CH2:18][O:19][C:20]1[CH:30]=[CH:29][C:23]([CH:24](O)[C:25]([OH:27])=O)=[CH:22][CH:21]=1.Cl.[C:32](Cl)(=[O:34])[CH3:33]>C(O)(=O)C>[C:32]([O:16][CH2:17][CH2:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([CH:24]2[C:7]3[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=3[O:15][C:25]2=[O:27])=[CH:29][CH:30]=1)(=[O:34])[CH3:33]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 73112,4-Di-tert-butylphenolHCID 199304444-(2-Hydroxyethoxy)mandelic acid2×

Produkt 1

HCID 102026063-[4-(2-Acetoxyethoxy)phenyl]-5,7-di-tert-butylbenzofuran-2-oneAusbeute 197,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A suspension of 154.7 g (0.75 mol) of 2,4-di-tert-butylphenol and 106.1 g (0.50 mol) of 4-(2-hydroxyethoxy)mandelic acid (compound (201), Example 10, Table 2) in 200 ml of acetic acid saturated with hydrogen chloride gas stirred under a nitrogen atmosphere is refluxed for 8 hours. The acetic acid is then distilled off on a vacuum rotary evaporator, 15 ml (0.21 mol) of acetyl chloride are added to the residue, and the mixture is maintained at 120° C. for 20 minutes. The reaction mixture is again concentrated on a vacuum rotary evaporator, 400 ml of methanol are added to the residue, and the mixture is allowed to stand at about -8° C. The precipitated crystals are filtered off, washed with 250 ml of cold methanol and dried to give 176.3 g (83%) of 3-[4-(2-acetoxyethoxy)phenyl]-5,7-di-tert-butylbenzofuran -2-one, m.p. 93°-96° C. (compound (101), Table 1). Recrystallization from ligroin yields the compound (101) in two crystal forms. Crystal form A: m.p. 75°-78° C., enthalpy of fusion 62.4 Joule/g. Crystal form B: m.p. 93°-96° C., enthalpy of fusion 118.2 Joule/g.

Aufarbeitung

  1. temperatureis refluxed for 8 hours
  2. additionare added to the residue
  3. concentrationThe reaction mixture is again concentrated on a vacuum rotary evaporator, 400 ml of methanol
  4. additionare added to the residue
  5. customto stand at about -8° C
  6. filtrationThe precipitated crystals are filtered off
  7. washwashed with 250 ml of cold methanol
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-1d53a3c9165447b29b0e746457ab7eda
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428162

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