3-Methoxybenzoic Acid → (3-Methoxyphenyl)(phenyl)methanone

HRID 2284830Notes

Reaction equation

HRID 2284830 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=O.[Al].[Cl-].[Cl-].[Cl-].[Al+3]>C1C=CC=CC=1.CCOC(C)=O>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([C:12]([C:9]2[CH:10]=[CH:11][CH:15]=[CH:16][CH:17]=2)=[O:14])[CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 114613-Methoxybenzoic AcidHCID 24819Phosphorus pentachlorideHCID 5359268AluminumHCID 6451240Aluminum(III) Chloride

Product 1

HCID 12451863(3-Methoxyphenyl)(phenyl)methanoneYield 151.5%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
10 °C

Procedure

To the mixture of phosphorus pentachloride (3763 g, 18.1 mol) in 7.5 L of benzene, 3-methoxy benzoic acid (2500 g, 16.4 mol) was added in portions. The mixture was stirred for 50 minutes until it became homogenous. The formation of the acid chloride was controlled by TLC. After completion, the mixture was cooled down to 10° C., reactor was covered with aluminum foil and aluminium trichloride (4820 g, 36.1 mol) was added in portions (internal temperature was held up to 30° C. maximum). Stirring was continued for 18 hours at RT. The reaction was monitored by TLC (AcOEt:hex 1:9). After completion, the reaction mixture was poured into ice and was diluted with AcOEt (7 L). Then organic layer was separated and the aqueous layer was extracted with AcOEt (2×10 L, 1×6 L). The combined organic layers were washed with water (5×3 L) to pH-6-7, saturated aqueous sodium hydrogen carbonate solution (15 L), dried (sodium sulfate), filtered and the solvent evaporated at reduced pressure to give a crude oil. The product was purified by vacuum distillation (130-139° C., 2 mbar) to obtain title compound (2637 g, 76%) as a pale yellow oil.

Workup

  1. additionwas added in portions
  2. additionwas added in portions (internal temperature
  3. customwas held up to 30° C.
  4. stirringStirring
  5. waitwas continued for 18 hours at RT
  6. additionAfter completion, the reaction mixture was poured into ice
  7. customThen organic layer was separated
  8. extractionthe aqueous layer was extracted with AcOEt (2×10 L, 1×6 L)
  9. washThe combined organic layers were washed with water (5×3 L) to pH-6-7, saturated aqueous sodium hydrogen carbonate solution (15 L)
  10. dry with materialdried (sodium sulfate)
  11. filtrationfiltered
  12. customthe solvent evaporated at reduced pressure
  13. customto give a crude oil
  14. distillationThe product was purified by vacuum distillation (130-139° C., 2 mbar)

Sources & evidence

ORD record
ord-e34b2b4e18504979a824c6f96ecb08fb
Source dataset
uspto-grants-2015_09
Patent number
US09145409B2

Reaction notes

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