HCID 22935584, compound → HCID 57096708, compound

HRID 1850382Notes

Reaction equation

HRID 1850382 reaction equation
[CH3:1][C:2]([O:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[C:9]=1[CH3:16])([CH3:6])[C:3]([OH:5])=O>O>[CH3:6][C:2]1([CH3:1])[C:3](=[O:5])[C:13]2[C:12]([CH3:14])=[CH:11][C:10]([CH3:15])=[C:9]([CH3:16])[C:8]=2[O:7]1

Participants

3

Reactant 1

HCID 22935584HCID 22935584, compound

Product 1

HCID 57096708HCID 57096708, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Polyphosphoric acid (1.5 kg) was added to 2-methyl-2-(2,3,5-trimethylphenoxy)propanoic acid (226 g, 1.02 mol) synthesized in Reference Example 34, and the mixture was stirred at 70° C. After reaction for 2 hours, the resulting mixture was poured into iced water and extracted using ethyl acetate. The extract was washed with 0.5 N sodium hydroxide aqueous solution and saturated saline, and dried using anhydrous magnesium sulfate. The solvent was removed under reduced pressure. Methanol was added to the residue, and the generated crystals were collected by filtration to give 164 g of the title compound (yield: 79%).

Workup

  1. customsynthesized in Reference Example 34
  2. customAfter reaction for 2 hours
  3. extractionextracted
  4. washThe extract was washed with 0.5 N sodium hydroxide aqueous solution and saturated saline
  5. customdried
  6. customThe solvent was removed under reduced pressure
  7. additionMethanol was added to the residue
  8. filtrationthe generated crystals were collected by filtration

Sources & evidence

ORD record
ord-2b9ccc88acb441c4a8e0bc853c4a91f2
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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