Phthalic Anhydride → 4',5'-Dimethylfluorescein

HRID 585768Notes

Reaction equation

HRID 585768 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[CH3:12][C:13]1[C:19]([OH:20])=[CH:18][CH:17]=[CH:16][C:14]=1[OH:15]>Cl.[Cl-].[Cl-].[Zn+2]>[CH3:12][C:13]1[C:14]2[O:15][C:19]3[C:13]([CH3:12])=[C:14]([OH:15])[CH:16]=[CH:17][C:18]=3[C:4]3([O:6][C:1](=[O:11])[C:2]4[C:3]3=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:16]=2[CH:17]=[CH:18][C:19]=1[OH:20]

Participants

5

Reactant 2

HCID 6811Phthalic AnhydrideHCID 118432-Methylresorcinol

Product 1

HCID 30829374',5'-Dimethylfluorescein

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
230 °C

Procedure

In a round bottom flask, phthalic anhydride (16.7 g, 113 mmol) and 2-methylresorcinol (24.9 g, 201 mmol) were combined and melted into a brown liquid at 150° C. Fused ZnCl2 (15 g, 110 mmol) was added over 40 min, and the temperature was slowly increased to 230° C. until all material solidified. The brick red solid was pulverized and boiled in 6M HCl for 30 min. The red solid was collected on a glass frit, washed with water, and dried in air over night (yield: 32.62 g, 91% of the theoretical yield).

Workup

  1. custommelted into a brown liquid at 150° C
  2. customThe red solid was collected on a glass frit
  3. washwashed with water
  4. customdried in air over night (yield: 32.62 g, 91% of the
  5. customtheoretical yield)

Sources & evidence

ORD record
ord-aef7bc4c9a1644189b3d0f19c73a80b8
Source dataset
uspto-grants-2005_08
Patent number
US06933384B2

Reaction notes

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