Acetic Acid → 2-(Tritylthio)acetic acid

HRID 652747Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 652747
[SH:1][CH2:2][C:3]([OH:5])=[O:4].[C:6]1([C:12]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)O)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(O)(=O)C.B(F)(F)F.CCOCC>O>[C:6]1([C:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[S:1][CH2:2][C:3]([OH:5])=[O:4])[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 1133Thioglycolic AcidHCID 6457TriphenylcarbinolHCID 8000Boron trifluoride etherate

Produkt 1

HCID 42453062-(Tritylthio)acetic acidAusbeute 64.574,199 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of distilled mercaptoacetic acid (20.87 g, 0.23 mmol), triphenylmethanol (60.0 g, 0.23 mol) and glacial acetic acid (200 ml) was heated to 70° C. Boron trifluoride etherate (32 ml, 0.25 mol) was added and the resulting brown mixture was stirred for 45 minutes at room temperature. The reaction mixture was then poured into water (500 ml), depositing a buff, granular solid which was filtered off, washed well with water then ether, and dried to give compound (V) (49.67 g, 67%). A further crop (12.27 g, 16%) was recovered from the ether washings, purified by recrystallization from benzene/hexanes. Both crops were homogeneous by TLC, mp 158.5°-160°.

Aufarbeitung

  1. filtrationwas filtered off
  2. washwashed well with water
  3. dry with materialether, and dried

Quellen und Nachweise

ORD-Eintrag
ord-72c720d74f6d464faa1d86a674086f23
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04673562

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