HCID 22456975, compound → HCID 22457004, compound

HRID 377752Notes

Reaction equation

HRID 377752 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH2:5][CH:6]([CH3:10])[C:7]([OH:9])=O>O>[F:1][C:2]1[CH:3]=[C:4]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[C:7](=[O:9])[CH:6]([CH3:10])[CH2:5]2

Participants

3

Reactant 1

HCID 22456975HCID 22456975, compound

Product 1

HCID 22457004HCID 22457004, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 3-fluoro-α-methyl-4-methoxy dihydrocinnamic acid, (49.3 g, 0.23 mol) in polyphosphoric acid (500 g) is heated at 95° C. on a steam bath with occasional agitation for 75 min. The dark red solution is stirred with water (3.0 l) overnight. The precipitate is collected, and is washed thoroughly with water. Its solution in ether is extracted with aqueous potassium bicarbonate (4×), is diluted with methylene chloride, is dried (MgSO4), and is evaporated. The residue is recrystallized from methylene chloride/hexanes to give 5-fluoro-6-methoxy-2-methylindanone (m.p. 76-78°).

Workup

  1. customThe precipitate is collected
  2. washis washed thoroughly with water
  3. extractionIts solution in ether is extracted with aqueous potassium bicarbonate (4×)
  4. additionis diluted with methylene chloride
  5. dry with materialis dried (MgSO4)
  6. customis evaporated
  7. customThe residue is recrystallized from methylene chloride/hexanes

Sources & evidence

ORD record
ord-78180b3e6c0c4afe9a4af8aef3cb81ad
Source dataset
uspto-grants-2000_02
Patent number
US06028116

Reaction notes

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