HCID 13066673, compound → HCID 13066674, compound

HRID 1163978Notes

Reaction equation

HRID 1163978 reaction equation
C[O:2][C:3]1[C:8]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16]C)=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:18][C:19]([OH:21])=[O:20]>I.C(OC(=O)C)(=O)C>[OH:2][C:3]1[C:8]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[OH:16])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:18][C:19]([OH:21])=[O:20]

Participants

4

Reactant 1

HCID 13066673HCID 13066673, compound

Product 1

HCID 13066674HCID 13066674, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 7918Acetic AnhydrideSolventHCID 24841Hydrogen iodideSolvent

Procedure

2-[2-Methoxy-3-(2-methoxyphenoxy)phenyl]acetic acid (10.50 g) was dissolved in a mixture of 48% hydriodic acid (61.5 ml) and acetic anhydride (31.5 ml) and then refluxed under heating for 40 minutes. After cooling, the reaction mixture was evaporated, and the residue was extracted with diethyl ether. The extract was washed with an aqueous sodium hydrogen sulfite and subsequently with saline, dried over magnesium sulfate and then evaporated. The oily residue (11.50 g) was allowed to stand, and the precipitating crystals (11.50 g) were recrystallized from benzene to give colorless crystals of 2-[2-hydroxy-3-(2-hydroxyphenoxy)phenyl]acetic acid (9.4 g). mp 91°-93° C.

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for 40 minutes
  3. temperatureAfter cooling
  4. customthe reaction mixture was evaporated
  5. extractionthe residue was extracted with diethyl ether
  6. washThe extract was washed with an aqueous sodium hydrogen sulfite and subsequently with saline
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customthe precipitating crystals (11.50 g) were recrystallized from benzene

Sources & evidence

ORD record
ord-32c81896caab4b50bff6a6c2d0959dd5
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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