Toluene → (2-Hydroxymethyl-2-adamantyl)-methyl methacrylate

HRID 555203

Reaktionsgleichung

Reaktionsgleichung von HRID 555203
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[C:2]1([CH2:13][OH:14])[CH2:11][OH:12])[CH2:8]2.[C:15](O)(=[O:19])[C:16]([CH3:18])=[CH2:17].C1(C)C=CC=CC=1>C(C1C(O)=C(C(C)(C)C)C=C(C)C=1)C1C(O)=C(C(C)(C)C)C=C(C)C=1.O>[C:15]([O:14][CH2:13][C:2]1([CH2:11][OH:12])[CH:1]2[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]1[CH2:4]3)[CH2:8]2)(=[O:19])[C:16]([CH3:18])=[CH2:17]

Komponenten

6

Edukt 3

HCID 1140TolueneHCID 4093Methacrylic AcidHCID 578740082,2-Adamantane dimethanol

Produkt 1

HCID 57874004(2-Hydroxymethyl-2-adamantyl)-methyl methacrylateAusbeute 33,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83982,2'-Methylenebis(4-methyl-6-tert-butylphenol)KatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 100 g of 2,2-adamantane dimethanol, 48.2 g of methacrylic acid, 20 g of toluene, 25 g of acidic ion-exchange resin Amberlist-15, and 0.1 g of 2,2′-methylenebis(6-t-butyl-p-cresol) was heated at 120° C. for 6 hours while the water being formed was azeotroped off. After the reaction mixture resumed room temperature, it was filtered through Celite. The filtrate was concentrated in vacuum. 300 g of hexane was added to the concentrate for recrystallization. The crystals were recovered and dried in vacuum, obtaining 45.0 g (yield 33%) of the target compound. The spectral data of this compound were identical with those of the product in Synthesis Example 1-2.

Aufarbeitung

  1. customformed
  2. customwas azeotroped off
  3. customresumed room temperature
  4. filtrationit was filtered through Celite
  5. concentrationThe filtrate was concentrated in vacuum
  6. addition300 g of hexane was added to the
  7. concentrationconcentrate for recrystallization
  8. customThe crystals were recovered
  9. customdried in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-9994c5174ff247b68a5989b22d92ca4d
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08053165B2

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