Aluminum(III) Chloride → HCID 18518301, compound

HRID 2299195Notes

Reaction equation

HRID 2299195 reaction equation
[CH2:1]([C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[CH2:16][C:17]([OH:19])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-]>C1C=CC=CC=1.S(Cl)(Cl)=O.C(Cl)Cl>[CH3:15][O:14][C:12]1[CH:11]=[CH:10][C:9]2[CH2:16][C:17](=[O:19])[C:7]3[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=3[CH2:1][C:8]=2[CH:13]=1

Participants

6

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 12743495HCID 12743495, compound

Product 1

HCID 18518301HCID 18518301, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 2-benzyl-4-methoxyphenylacetic acid (14.2 g, 0.055 m) in benzene (120 mL) and thionyl chloride (28 mL) was refluxed for 1 hour and concentrated. The acid chloride was dissolved in dry methylene chloride (40 mL), and the solution was added dropwise under argon to a solution of AlCl3 (14.7 g, 0.11 mol) in methylene chloride (600 mL). The reaction was stirred under an argon atmosphere for 2.5 hours at room temperature, then was quenched with ice-water (200 mL). The layers were separated, and the organic phase was washed sequentially with 10% NaOH solution, water, and dil. HCl. The resulting solution was diluted with ether (200 mL), dried over MgSO4, and concentrated. The solid residue was triturated with ether/hexane (1:1) and 9.35 g of the title compound was collected by filtration: Mp 105-106° C.; 1H NMR (400 MHz, CDCl3) δ3.72 (s, 3H), 4.1 (s, 2H), 4.2 (s, 2H), 6.7 (d, 1H), 6.82 (s, 1H), 7.30 (m, 4H), 8.1 (d, 1H).

Workup

  1. concentrationconcentrated
  2. dissolutionThe acid chloride was dissolved in dry methylene chloride (40 mL)
  3. customwas quenched with ice-water (200 mL)
  4. customThe layers were separated
  5. washthe organic phase was washed sequentially with 10% NaOH solution, water, and dil. HCl
  6. additionThe resulting solution was diluted with ether (200 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe solid residue was triturated with ether/hexane (1:1) and 9.35 g of the title compound
  10. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-30f0e67357a942f4b6fd861fbcd525c8
Source dataset
uspto-grants-2002_12
Patent number
US06495560B1

Reaction notes

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