Aluminum(III) Chloride → HCID 19591954, compound

HRID 1369228Notes

Reaction equation

HRID 1369228 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=O)=[C:5]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:4]=1.[Al+3].[Cl-].[Cl-].[Cl-]>S(Cl)(Cl)=O.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[CH2:9][C:10](=[O:12])[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[O:13][C:5]=2[CH:4]=1

Participants

5

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 18518328HCID 18518328, compound

Product 1

HCID 19591954HCID 19591954, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 2-(4-methoxy-2-phenoxyphenyl)acetic acid (594 mg, 2.3 mmole) in thionyl chloride (10 mL) was heated at reflux for 30 min, then was concentrated to dryness, and the residue was reconcentrated from toluene. The resulting residue was dissolved in dry CH2Cl2 (3 mL), and the solution was added dropwise at RT to a suspension of AlCl3 (673 mg, 5.06 mmole) in dry CH2Cl2 (4 mL) in a flame-dried flask under argon. After stirring for 2.5 hr, the mixture was diluted with CH2Cl2 (10 mL) and washed sequentially with 1.0 N NaOH and brine. Drying (MgSO4), concentration, and flash chromatography on silica gel (5% EtOAc/hexanes) gave the title compound (264 mg, 48%) as a light yellow oil: 1H NMR (300 MHz, CDCl3) δ3.80 (s, 3 H), 4.02 (s, 2 H), 6.74-8.08 (m, 7 H).

Workup

  1. temperatureat reflux for 30 min
  2. concentrationwas concentrated to dryness
  3. dissolutionThe resulting residue was dissolved in dry CH2Cl2 (3 mL)
  4. washwashed sequentially with 1.0 N NaOH and brine
  5. customDrying
  6. concentration(MgSO4), concentration, and flash chromatography on silica gel (5% EtOAc/hexanes)

Sources & evidence

ORD record
ord-976b7b9140ca4dceb27def80641de961
Source dataset
uspto-grants-2003_06
Patent number
US06576643B2

Reaction notes

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