Phthalic Anhydride → HCID 86674072, compound

HRID 576470Notes

Reaction equation

HRID 576470 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:18])[C:14]([F:17])([F:16])[F:15].[C:19]1(=[O:29])[O:24][C:22](=[O:23])[C:21]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]12.[Cl-].[Al+3].[Cl-].[Cl-]>ClC(Cl)C>[OH:8][C:6]1[CH:7]=[C:2]([OH:1])[C:3]([CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:18])[C:14]([F:15])([F:16])[F:17])=[CH:4][C:5]=1[C:19]([C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22]([OH:24])=[O:23])=[O:29]

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 6451240Aluminum(III) ChlorideHCID 86674073HCID 86674073, compound

Product 1

HCID 86674072HCID 86674072, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of 4 (0.56 g, 2.1 mmol), phthalic anhydride (0.32 g, 2.2 mmol) and aluminum chloride (0.80 g, 6.0 mmol) was stirred in anhydrous dichloroethane (under argon) for 20 hr. The dichloroethane solvent was decanted away and the solid residue was dissolved in 50 ml of ethyl acetate and washed with 50 ml of water. The pH of the aqueous phase was adjusted to approximately pH 3 by addition of acetic acid and then extracted with ethyl acetate (2×50 ml). The combined organic extracts were dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography eluting with a gradient of 25-0% hexane in ethyl acetate. The pure product fractions were evaporated affording a homogenous oil: 0.32 g (34% yield).

Workup

  1. customThe dichloroethane solvent was decanted away
  2. dissolutionthe solid residue was dissolved in 50 ml of ethyl acetate
  3. washwashed with 50 ml of water
  4. additionThe pH of the aqueous phase was adjusted to approximately pH 3 by addition of acetic acid
  5. extractionextracted with ethyl acetate (2×50 ml)
  6. dry with materialThe combined organic extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by silica gel chromatography
  10. washeluting with a gradient of 25-0% hexane in ethyl acetate
  11. customThe pure product fractions were evaporated
  12. customaffording a homogenous oil

Sources & evidence

ORD record
ord-4a7482fd4746485880dcb287f56e0b17
Source dataset
uspto-grants-2015_05
Patent number
US09040307B2

Reaction notes

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