Toluene → HCID 86617042, compound

HRID 2113251Notes

Reaction equation

HRID 2113251 reaction equation
[C:1]1(C)[CH:6]=[CH:5][C:4]([S:7]([O:10][C:11](=[O:25])[CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.O.[C:28]1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1.C1(C(C2C=CC=CC=2)=C=O)C=CC=CC=1>C(OCC)C>[C:5]1([CH3:28])[C:4]([S:7]([O:10][C:11](=[O:25])[CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)(=[O:9])=[O:8])=[CH:3][CH:2]=[CH:1][CH:6]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 123069Diphenylketene2×HCID 521998p-Toluenesulfonic acid monohydrateHCID 86617043HCID 86617043, compound

Product 1

HCID 86617042HCID 86617042, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
22.5 °C

Procedure

The preparation of diphenylacetyl p-toluenesulfonate. A 100-mL, flask equipped with a magnetic stirring bar and Dean-Stark apparatus was charged with p-toluenesulfonic acid monohydrate (9.51 g, 0.05 mol) and toluene (60 mL). The mixture was refluxed for 2 h to remove water and toluene was distilled off to 10 mL volume at normal pressure. This residue was cooled to 20-25° C. and added dropwise to a stirred solution of diphenylketene (9.7 g, 0.05 mol) in anhydrous diethylether (20 mL) at 0-5° C. over 3-5 min. The orange solution of diphenylketene became slightly yellow; the reaction mixture was stirred for 6 h at 0-5° C. The formed precipitate was filtered under a nitrogen atmosphere, washed with anhydrous diethyl ether (15 mL) and dried in a nitrogen flow giving diphenylacetyl toluenesulphonate (12.3 g, 67%), as off white prisms, m.p. 84-87° C. (decomposition). 1H NMR (CDCl3) δ 2.43 (s, 3H), 5.01 (s, 1H), 7.10-7.16 (m, 4H), 7.24-7.32 (m, 8H), 7.82 (d, J=7.9 Hz, 2H); 13C NMR (CDCl3) δ 21.7, 57.0, 127.8, 128.4, 128.8, 129.0, 129.6, 132.6, 136.2, 146.0, 165.5. Anal. Calcd. for C21H18O4S (366.44): C, 68.83; H, 4.95. Found: C, 68.61; H, 4.89.

Workup

  1. customA 100-mL, flask equipped with a magnetic stirring bar
  2. temperatureThe mixture was refluxed for 2 h
  3. customto remove water and toluene
  4. distillationwas distilled off to 10 mL volume at normal pressure
  5. filtrationThe formed precipitate was filtered under a nitrogen atmosphere
  6. washwashed with anhydrous diethyl ether (15 mL)
  7. customdried in a nitrogen flow

Sources & evidence

ORD record
ord-49d675aee727401986372205dbeb1401
Source dataset
uspto-grants-2009_04
Patent number
US07524990B2

Reaction notes

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