P-Toluic Acid → 4-Methylbenzoyl Chloride

HRID 1482443Notes

Reaction equation

HRID 1482443 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[CH:6][CH:7]=1.S(Cl)([Cl:13])=O>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([Cl:13])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7470P-Toluic Acid2×HCID 24386Thionyl Chloride2×

Product 1

HCID 134054-Methylbenzoyl Chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

p-Toluic acid (100 g, 0.734 mol) (Tokyo Chemical Industry Co., Ltd.) and toluene (500 mL) (Wako Pure Chemical Industries, Ltd.) were placed into a sufficiently dried recovery flask (egg plant flask), and p-toluic acid was dissolved. Thionyl chloride (132.4 mL, 1.84 mol) (Wako Pure Chemical Industries, Ltd.) was added dropwise to this solution for 1 hour. After the dropwise addition, the solution was heated and refluxed for 2 hours. After the reaction, the temperature was cooled to room temperature, and then remaining thionyl chloride and remaining toluene were evaporated by using a rotary evaporator. Toluene (200 mL) was added to an obtained concentrate, and the concentrating operation was repeated twice. A finally obtained residue was dissolved in tetrahydrofuran (200 mL) (Wako Pure Chemical Industries, Ltd.), which was used in the next step.

Workup

  1. dissolutionwas dissolved
  2. additionAfter the dropwise addition
  3. temperaturethe solution was heated
  4. temperaturerefluxed for 2 hours
  5. customAfter the reaction
  6. customwere evaporated
  7. customa rotary evaporator
  8. additionToluene (200 mL) was added to an obtained
  9. concentrationconcentrate
  10. dissolutionA finally obtained residue was dissolved in tetrahydrofuran (200 mL) (Wako Pure Chemical Industries, Ltd.)

Sources & evidence

ORD record
ord-a2d1f1330b094a11af189b019ca2e5d6
Source dataset
uspto-grants-2016_08
Patent number
US09414998B2

Reaction notes

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