Hydrochloric Acid → Benzophenone, 3-methoxy-4'-methyl-

HRID 1912340Notes

Reaction equation

HRID 1912340 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5](Cl)(=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=1.[C:16]1([CH3:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>C(Cl)Cl>[CH3:22][C:16]1[CH:21]=[CH:20][C:19]([C:5]([C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=2)=[O:14])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 74374m-Anisoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 54881Benzophenone, 3-methoxy-4'-methyl-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of AlCl3 (1.1 equivalents) in CH2Cl2 (40 ml) a solution of m-anisoylchloride (12.0 g) and toluene (1 equivalent) in CH2Cl2 (10 ml) is dropwise added. The resulting mixture is stirred at room temperature for 4 hours, then poured into 200 ml of a mixture ice-37% by weight HCl (1/1 v/v). The organic phase and the aqueous phase are separated. The organic phase is dehydrated with sodium sulphate. Filtration is then effected and the organic solvent evaporated. 4-methyl-3′-methoxybenzophenone is obtained. Yield: quantitative. IR (nujol) (λ=cm−1) 1690 (C═O); 1H-NMR (CDCl3) δ 2.44 (s, 3H); 3.86 (s, 3H); 7.08-7.18 (m, 1H); 7.20-7.40 (m, 5H); 7.73 (d, 2H, J=8.4 Hz). Anal. calc. for C15H14O2: C, 79.62; H, 6.24. Found: C, 79.53; H, 6.22.

Workup

  1. additionis dropwise added
  2. customThe organic phase and the aqueous phase are separated
  3. filtrationFiltration
  4. customthe organic solvent evaporated

Sources & evidence

ORD record
ord-b20822c850c64a128ec02f141e30b807
Source dataset
uspto-grants-2013_12
Patent number
US08609659B2

Reaction notes

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