HCID 64853602, compound → HCID 55275761, compound

HRID 1774583Notes

Reaction equation

HRID 1774583 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:3]=1[O:4][CH2:5][CH2:6][C:7]([OH:9])=O>O>[F:1][C:2]1[C:3]2[O:4][CH2:5][CH2:6][C:7](=[O:9])[C:10]=2[C:11]([CH3:14])=[CH:12][CH:13]=1

Participants

3

Reactant 1

HCID 64853602HCID 64853602, compound

Product 1

HCID 55275761HCID 55275761, compoundYield 68,534.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-(2-fluoro-5-methylphenoxy)propanoic acid (10a) (860 mg, 4.64 mmol) in polyphosphoric acid (12.8 g, 130.3 mmol) was stirred at 100° C. for 2 hours. After cooling to room temperature, the mixture was diluted with water (90 mL), and extracted with ethyl acetate (2×60 mL). The organic layers were combined, washed with brine, dried over sodium sulfate, and concentrated in vacuo to provide 8-fluoro-5-methyl-3,4-dihydro-2H-1-benzopyran-4-one (10b) (573 mg, 3.18 mol, 73%) which was used without further purification. Ms m/z ([M+H]+) 181.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate (2×60 mL)
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fce78b70cc514ef89c14ef08f2bff1b0
Source dataset
uspto-grants-2016_02
Patent number
US09260395B2

Reaction notes

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