Hydrochloric Acid → p-Cresol benzoate

HRID 1042525Notes

Reaction equation

HRID 1042525 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([CH3:8])[CH:2]=1.[C:9](Cl)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl>N1C=CC=CC=1>[C:9]([O:7][C:6]1[CH:5]=[CH:4][C:3]([CH3:8])=[CH:2][CH:1]=1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2879P-CresolHCID 7412Benzoyl chloride

Product 1

HCID 11962p-Cresol benzoateYield 92%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 65.0 g (0.60 mol) of p-cresol, 92.7 g (0.66 mol) of benzoyl chloride, and 6 mL of anhydrous pyridine was refluxed for 1.5 hr and then added to 600 mL of 2% hydrochloric acid. The product was extracted with 2×100 mL of ether, the combined extract was washed by 2% NaOH, then dried over Na2SO4, and evaporated to dryness. Drying the residue in vacuum gave 117 g (92%) of p-tolyl benzoate (bp 127-135° C./25 mm Hg). A mixture of 117 g (0.552 mol) of p-tolyl benzoate and 92.0 (0.689 mol) of AlCl3 was slowly (for ca. 0.5 hr) heated to 120-125° C. This mixture was stirred at this temperature for 1 hr, and then 1000 mL of 2M HCl was added at 0° C. The product was extracted with 3×200 mL of diethyl ether, the combined extract was dried over Na2SO4 and then evaporated to dryness. This procedure gave 116 g (99%) of the title product which was further used without an additional purification.

Workup

  1. temperaturewas refluxed for 1.5 hr
  2. extractionThe product was extracted with 2×100 mL of ether
  3. extractionthe combined extract
  4. washwas washed by 2% NaOH
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness
  7. customDrying the residue in vacuum

Sources & evidence

ORD record
ord-68d049dc6f5347d99d64c7249c5a2995
Source dataset
uspto-grants-2013_10
Patent number
US08557936B2

Reaction notes

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