HCID 54411900, compound → HCID 12395569, compound

HRID 1287474Notes

Reaction equation

HRID 1287474 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9](=[O:20])[C:10](=[CH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:11][CH3:12])[CH:5]=[CH:4][C:3]=1[O:21][CH3:22]>FC(F)(F)C(O)=O>[CH2:11]([CH:10]1[CH:13]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:5]2[C:6](=[C:7]([Cl:8])[C:2]([Cl:1])=[C:3]([O:21][CH3:22])[CH:4]=2)[C:9]1=[O:20])[CH3:12]

Participants

3

Reactant 1

HCID 54411900HCID 54411900, compound

Product 1

HCID 12395569HCID 12395569, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2,3-Dichloro-4-(2-benzylidenebutyryl)anisole (111.0 g., 0.331 mole) and trifluoroacetic acid (350 ml.) are heated at gentle reflux for 70 hours. The trifluoroacetic acid is removed, the oily residue triturated with ether to give 88.1 g. (80%) of 2-ethyl-3-phenyl-6,7-dichloro-5-methoxy-1-indanone which on crystallization from benzene melts at 141°-143° C.

Workup

  1. temperatureat gentle reflux for 70 hours
  2. customThe trifluoroacetic acid is removed
  3. customthe oily residue triturated with ether
  4. customto give 88.1 g
  5. custom(80%) of 2-ethyl-3-phenyl-6,7-dichloro-5-methoxy-1-indanone which on crystallization from benzene melts at 141°-143° C.

Sources & evidence

ORD record
ord-e79f3e0f4b8c4c67a86319a10a0e572a
Source dataset
uspto-grants-1976_10
Patent number
US03984465

Reaction notes

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