Hydrochloric Acid → 5-(1,1-Dimethylethyl)-2-hydroxy-1,3-benzenedimethanol

HRID 127661

Reaktionsgleichung

Reaktionsgleichung von HRID 127661
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-:12].[Na+].[CH2:14]=[O:15].Cl.[CH:17](Cl)(Cl)Cl>C(O)(=O)C.O>[CH2:17]([C:9]1[CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=[C:7]([CH2:14][OH:15])[C:8]=1[OH:11])[OH:12]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 6212ChloroformHCID 73934-tert-ButylphenolHCID 14798Sodium Hydroxide

Produkt 1

HCID 1509815-(1,1-Dimethylethyl)-2-hydroxy-1,3-benzenedimethanolAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

200 grams (1.331 moles) of para-t-butylphenol and 400 ml. of water were placed in a 2-liter, 3-neck, round bottom flask fitted with a thermometer, a stirrer and a dropping funnel. The flask was placed in a water bath, the contents stirred and 106.6 grams (1.331 moles) of 50% aq. NaOH added. The temperature of the resulting slurry was adjusted to 30° C. (by cooling) and 227 grams (~2.8 moles) of 37% formalin added. The mixture was heated to 60° C. and stirred at that temperature for 4 hours. It was then cooled to 35° C. and 444 ml. (1.331 moles) of 3 N aq. HCl were added. Enough dilute acetic acid was then added to make the mixture just acid. 100 ml. of chloroform was stirred in and the phases allowed to separate. The chloroform layer, containing essentially all of the product resin, was removed, washed once with water, dried by azeotropic distillation and stripped in vacuo. 276 grams (99% yield) of the title product was obtained as a resinous residue which crystallized on standing; equivalent wt. 220 grams per phenolic --OH (vs 212, theoretical).

Aufarbeitung

  1. customfitted with a thermometer, a stirrer and a dropping funnel
  2. customThe flask was placed in a water bath
  3. customwas adjusted to 30° C.
  4. additionadded
  5. stirringstirred at that temperature for 4 hours
  6. temperatureIt was then cooled to 35° C.
  7. customto separate
  8. additionThe chloroform layer, containing essentially all of the product resin
  9. customwas removed
  10. washwashed once with water
  11. customdried by azeotropic distillation

Quellen und Nachweise

ORD-Eintrag
ord-53502b33ddb74b629c44abc94f73fd7f
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04256844

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