Acetic Acid → 2-(Tritylthio)acetic acid

HRID 652747Notes

Reaction equation

HRID 652747 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 42453062-(Tritylthio)acetic acidYield 64,574.199%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

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°.

Workup

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

Sources & evidence

ORD record
ord-72c720d74f6d464faa1d86a674086f23
Source dataset
uspto-grants-1987_06
Patent number
US04673562

Reaction notes

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