Phthaloyl chloride → HCID 53968667, compound

HRID 568329Notes

Reaction equation

HRID 568329 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2].[C:17](Cl)(=[O:27])[C:18]1[C:19](=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:20](Cl)=[O:21]>O1CCCC1.CCCCCC>[C:12]([C:7]1[CH:8]=[C:9]([CH3:11])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[O:16][C:17](=[O:27])[C:18]1[C:19](=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:20]([O:16][C:6]1[C:7]([C:12]([CH3:13])([CH3:14])[CH3:15])=[CH:8][C:9]([CH3:11])=[CH:10][C:5]=1[C:1]([CH3:4])([CH3:3])[CH3:2])=[O:21])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 2

HCID 6955Phthaloyl chlorideHCID 314042,6-Di-tert-butyl-4-methylphenol

Product 1

HCID 53968667HCID 53968667, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a stirred, ice-cold solution of 11.6 g (0.05 mol) 2,6-di-tert-butyl-4-methylphenol in 100 mL dry tetrahydrofuran was added dropwise under argon 25 mL 23M n-butyllithium in hexane. After 2.5 hours, 5.3 g (0.026 mol) fresh phthaloyl chloride was added dropwise and the mixture stirred overnight at room temperature. Product was isolated by extraction, washed with ligroin and recrystallized from acetonitrile to give 4 g nearly pure Compound 6, as white crystals, m.p. 262°-5° C.

Workup

  1. customProduct was isolated by extraction
  2. washwashed with ligroin
  3. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-e86bd02bef364217ae612d9052846284
Source dataset
uspto-grants-1988_03
Patent number
US04728599

Reaction notes

Loading…