Phosphorus oxide (P4O10) → 5,6-Dimethoxy-1-indanone

HRID 1680497Notes

Reaction equation

HRID 1680497 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH2:25][CH2:26][C:27]([OH:29])=O)[CH:20]=[CH:21][C:22]=1[O:23][CH3:24]>C1C=CC=CC=1>[CH3:15][O:16][C:17]1[CH:18]=[C:19]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[C:27](=[O:29])[CH2:26][CH2:25]2

Participants

4

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 750193-(3,4-Dimethoxyphenyl)propionic acid

Product 1

HCID 750185,6-Dimethoxy-1-indanoneYield 46.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Phosphorus pentoxide (500 g, 3.5 mol) is added portionwise to a mechanically stirred solution of 3-(3,4-dimethoxyphenyl)propionic acid (100 g, 0.67 mol) in benzene (2500 ml) and the mixture is refluxed for 8 hr. The reaction is slowly poured into ice-water, and the benzene layer is separated and washed with 10% sodium hydroxide and water, dried and evaporated to give 5,6-dimethoxyindan-1-one (60 g), mp 100° C., described by W. H. Perkin and R. Robinson, J. Chem. Soc., 1073 (1907).

Workup

  1. temperaturethe mixture is refluxed for 8 hr
  2. customthe benzene layer is separated
  3. washwashed with 10% sodium hydroxide and water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-1a63ba7084b64b7ea931abff84055643
Source dataset
uspto-grants-1981_06
Patent number
US04273773

Reaction notes

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