Acetic Acid → Benzoic acid, 2-(2,7-dichloro-3,6-dihydroxy-9H-xanthen-9-yl)-

HRID 1879599Notes

Reaction equation

HRID 1879599 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]([O:9][C:10]3([C:23]4[C:18](=[CH:19][C:20]([OH:25])=[C:21]([Cl:24])[CH:22]=4)[O:17][C:16]4[C:11]3=[CH:12][C:13]([Cl:27])=[C:14]([OH:26])[CH:15]=4)[C:4]2=[CH:3][CH:2]=1)=[O:8].C(O)(=O)C>C1COCC1.[Zn]>[Cl:24][C:21]1[C:20]([OH:25])=[CH:19][C:18]2[O:17][C:16]3[C:11](=[CH:12][C:13]([Cl:27])=[C:14]([OH:26])[CH:15]=3)[CH:10]([C:4]3[CH:3]=[CH:2][CH:1]=[CH:6][C:5]=3[C:7]([OH:9])=[O:8])[C:23]=2[CH:22]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 649442′,7′-Dichlorofluorescein2×

Product 1

HCID 14598431Benzoic acid, 2-(2,7-dichloro-3,6-dihydroxy-9H-xanthen-9-yl)-

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

2′,7′-Dichlorofluorescein (2.0 g, 5.0 mmol) was dissolved in 80 mL of THF, containing 2 mL of acetic acid. Zn (powder, 8.0 g, 122 mmol) was added portionwise (0.5 g with ˜15 min intervals) to the solution of 2′,7′-Dichlorofluorescein. After all amount of Zn was added the reaction mixture was stirred overnight. All solids have been filtered off, washed with THF and evaporated. The residue was re-dissolved in ethyl acetate (120 mL) and washed with water (2×30 mL), brine (30 mL), dried over sodium sulfate and evaporated. The crude product (˜2.0 g, oil) was used for the next step without further purification.

Workup

  1. filtrationAll solids have been filtered off
  2. washwashed with THF
  3. customevaporated
  4. dissolutionThe residue was re-dissolved in ethyl acetate (120 mL)
  5. washwashed with water (2×30 mL), brine (30 mL)
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe crude product (˜2.0 g, oil) was used for the next step without further purification

Sources & evidence

ORD record
ord-56fa9a43deba4cb8880a2678ea7faf1a
Source dataset
uspto-grants-2012_11
Patent number
US08318450B2

Reaction notes

Loading…