O-Xylene → 5-Fluoro-2-methylindan-1-one

HRID 267822Notes

Reaction equation

HRID 267822 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH:9]([CH3:12])[CH2:10]O)=[CH:4][CH:3]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C1(C)C(C)=CC=CC=1>O>[F:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[C:8](=[O:13])[CH:9]([CH3:12])[CH2:10]2

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 14812Phosphorus oxide (P4O10)HCID 215218911-(4-Fluorophenyl)-3-hydroxy-2-methylpropan-1-one

Product 1

HCID 30162575-Fluoro-2-methylindan-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 18.2 g. (0.10 mole) of 4'-fluoro-3-hydroxy-2-methylpropiophenone and 12 g. of phosphorous pentoxide in 100 ml. of xylene is refluxed for one hour. The reaction is cooled, water is added and the xylene layer is washed with aqueous sodium hydroxide and water. The organic layer is then concentrated in vacuo to give 5-fluoro-2-methyl-1-indanone.

Workup

  1. additionA mixture of 18.2 g
  2. temperatureThe reaction is cooled
  3. washthe xylene layer is washed with aqueous sodium hydroxide and water
  4. concentrationThe organic layer is then concentrated in vacuo

Sources & evidence

ORD record
ord-e35a1b1b9bd74744aba18c195be0050a
Source dataset
uspto-grants-1976_03
Patent number
US03944600

Reaction notes

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