Pyridinium chloride → 2-Benzyl-2-methyl-5-hydroxy-6,7-dichloro-1-indanone

HRID 1287445Notes

Reaction equation

HRID 1287445 reaction equation
[CH2:1]([C:8]1([CH3:22])[CH2:16][C:15]2[C:10](=[C:11]([Cl:20])[C:12]([Cl:19])=[C:13]([O:17]C)[CH:14]=2)[C:9]1=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.N1C=CC=CC=1>O>[CH2:1]([C:8]1([CH3:22])[CH2:16][C:15]2[C:10](=[C:11]([Cl:20])[C:12]([Cl:19])=[C:13]([OH:17])[CH:14]=2)[C:9]1=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 123955662-Benzyl-2-methyl-5-methoxy-6,7-dichloro-1-indanone

Product 1

HCID 123955912-Benzyl-2-methyl-5-hydroxy-6,7-dichloro-1-indanoneYield 34.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

2-Benzyl-2-methyl-5-methoxy-6,7-dichloro-1-indanone (6 g.) is mixed with pyridine hydrochloride (60 g.) and the mixture is heated at 180°C. for three hours. The dark liquid is poured into water (1 l.) and the dark powdery product is collected and crystallized from acetic acid to obtain 2-benzyl-2-methyl-5-hydroxy-6,7-dichloro-1-indanone (2 g.), m.p. 219°-221°C. The product is identified by its nuclear magnetic resonance spectrum.

Workup

  1. customthe dark powdery product is collected
  2. customcrystallized from acetic acid

Sources & evidence

ORD record
ord-2802188bd2c648b0b30fe3a9a6d58051
Source dataset
uspto-grants-1976_10
Patent number
US03984465

Reaction notes

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