p-Toluenesulfonic acid → HCID 178451335, compound

HRID 603919Notes

Reaction equation

HRID 603919 reaction equation
[CH:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:5][CH:4]=1)=O.[F:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:18][C:19]1[CH:25]=[CH:24][C:22](/[N:23]=[CH:1]/[C:3]2[CH:17]=[CH:16][C:6]([O:7][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:5][CH:4]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 97314-FluoroanilineHCID 639902Tert-butyl 2-(4-formylphenoxy)acetate

Product 1

HCID 178451335HCID 178451335, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

tert-Butyl (4-formylphenoxy)acetate (93.7 g, 0.40 mol) was dissolved in dry toluene (200 mL), added 4-fluoroaniline (38.1 mL, 0.40 mol) and p-toluene sulfonic acid (cat, ˜1 g). The mixture was refluxed in a Dean-Stark apparatus for 2 hours, cooled at an icebath and a precipitate was formed. The precipitate was filtered, washed with cold heptane and dried to afford the title compound.

Workup

  1. temperatureThe mixture was refluxed in a Dean-Stark apparatus for 2 hours
  2. temperaturecooled at an icebath
  3. customa precipitate was formed
  4. filtrationThe precipitate was filtered
  5. washwashed with cold heptane
  6. customdried

Sources & evidence

ORD record
ord-5f6917bb578d45ed9e215d16d0400b98
Source dataset
uspto-grants-2011_03
Patent number
US07906502B2

Reaction notes

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