Naphthalene → HCID 70013449, compound

HRID 1369362Notes

Reaction equation

HRID 1369362 reaction equation
[Li:1].C1C2C(=CC=CC=2)C=CC=1.Cl[P:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH3:21][C:22]1[CH:30]=[C:29]([CH3:31])[CH:28]=[C:27]([CH3:32])[C:23]=1[C:24](Cl)=[O:25]>O1CCCC1>[CH3:21][C:22]1[CH:30]=[C:29]([CH3:31])[CH:28]=[C:27]([CH3:32])[C:23]=1[C:24]([PH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:25].[Li:1]

Participants

6

Reactant 4

HCID 931NaphthaleneHCID 12573Phenyl phosphorus dichlorideHCID 970382,4,6-Trimethylbenzoyl chlorideHCID 3028194Lithium

Product 1

HCID 70013449HCID 70013449, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
22.5 °C

Procedure

Under argon and with the exclusion of moisture, 14.0 g of lithium (2.0 mol) are introduced into 250 ml of tetrahydrofuran at room temperature. Following the addition of 1.25 g of naphthalene, 44.8 g (0.25 mol) of dichlorophenylphosphine are added dropwise with stirring at 20-25° C. and, after stirring for 4 h, the black solution is filtered into a three-necked round flask through a frit (G2 porosity) with the exclusion of moisture and under argon as a protective gas. 47.2 g (0.258 mol) of 2,4,6-trimethylbenzoyl chloride are added dropwise at room temperature over the course of 30 minutes with stirring and cooling. Stirring for 2 hours gives the title compound as a red solution in tetrahydrofuran.

Workup

  1. additionare added dropwise
  2. stirringafter stirring for 4 h
  3. filtrationthe black solution is filtered into a three-necked round flask through a frit (G2 porosity) with the exclusion of moisture and under argon as a protective gas
  4. stirringwith stirring
  5. temperaturecooling
  6. stirringStirring for 2 hours

Sources & evidence

ORD record
ord-d72a6a1e5665418b9f0041aa8042c3bf
Source dataset
uspto-grants-2003_06
Patent number
US06579663B2

Reaction notes

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