Phosphorus pentachloride → HCID 18518703, compound

HRID 1369018Notes

Reaction equation

HRID 1369018 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[Cl:7][C:8]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:9]=1[O:10][CH2:11][CH2:12][C:13]([OH:15])=O.[Cl-].[Al+3].[Cl-].[Cl-]>C1C=CC=CC=1>[Cl:7][C:8]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]2[C:9]=1[O:10][CH2:11][CH2:12][C:13]2=[O:15]

Participants

5

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 6451240Aluminum(III) ChlorideHCID 18518707HCID 18518707, compound

Product 1

HCID 18518703HCID 18518703, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Phosphorous pentachloride (1.3 g; 6.2 mmol) was added to a suspension of 3-(2-chloro-4-methoxyphenoxy)propionic acid (0.85 g; 3.7 mmol; from step (ii) above) in benzene (10 mL). The resultant clear solution was heated quickly to boiling and then cooled on an ice bath. Aluminium chloride (1.5 g; 11 mmol) was added in portions and, after complete addition, ice water was added. Extraction with ether, washing of the organic layer with NaHCO3/aq. and NaOH (2M; aq.), drying (Na2SO4) and concentration yielded 0.73 g (93%) of the sub-title compound.

Workup

  1. temperatureThe resultant clear solution was heated quickly
  2. temperaturecooled on an ice bath
  3. additionwas added
  4. extractionExtraction with ether
  5. washwashing of the organic layer with NaHCO3/aq
  6. dry with materialand NaOH (2M; aq.), drying
  7. concentration(Na2SO4) and concentration

Sources & evidence

ORD record
ord-f53790968213499baebf64244cae49b3
Source dataset
uspto-grants-2003_06
Patent number
US06576657B2

Reaction notes

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