1-Indanone → 6-Methoxy-2-methyl-2,3-dihydro-1H-inden-1-one

HRID 47635

Reaction equation

HRID 47635 reaction equation
[CH3:1][CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)[C:3]([OH:5])=O.C1(=O)C2C(=CC=CC=2)CC1>O>[CH3:14][O:13][C:10]1[CH:11]=[C:12]2[C:7]([CH2:6][CH:2]([CH3:1])[C:3]2=[O:5])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 67351-IndanoneHCID 105358043-(4-Methoxyphenyl)-2-methylpropanoic acid

Product 1

HCID 2311786-Methoxy-2-methyl-2,3-dihydro-1H-inden-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Alternatively, the same compound can be obtained by adding α-methyl-β-(p-methoxylphenyl)propionic acid (15 g.) to 170 g. of polyphosphoric acid at 50° and heating the mixture at 83-90° for two hours. The syrup is poured into iced water. The mixture is stirred for one-half hour, and is extracted with ether (3×). The etheral solution is washed with water (2×) and 5% NaHCO3 (5×) until all acidic material has been removed, and is dried over sodium sulfate. Evaporation of the solution gives 9.1 g. of the indanone as a pale yellow oil.

Workup

  1. customAlternatively, the same compound can be obtained
  2. extractionis extracted with ether (3×)
  3. washThe etheral solution is washed with water (2×) and 5% NaHCO3 (5×) until all acidic material
  4. customhas been removed
  5. dry with materialis dried over sodium sulfate
  6. customEvaporation of the solution
  7. customgives 9.1 g

Sources & evidence

ORD record
ord-13733782053640fcb7c2da9358d93fcf
Source dataset
uspto-grants-2004_03
Patent number
US06699894B1

Linked notes

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