Benzene → HCID 69244216, compound

HRID 885470Notes

Reaction equation

HRID 885470 reaction equation
[C:1]1([C:18]([OH:20])=O)[C:14]2[CH2:13][C:12]3[CH:11]=[CH:10][CH:9]=[C:8]([C:15]([OH:17])=O)[C:7]=3[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[Al+3].[Cl-].[Cl-].[Cl-].[CH:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Cl>CN(C)C=O.S(Cl)(Cl)=O>[C:18]([C:1]1[C:14]2[CH2:13][C:12]3[C:7](=[C:8]([C:15](=[O:17])[C:1]4[CH:14]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH:9]=[CH:10][CH:11]=3)[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1)(=[O:20])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 69239993HCID 69239993, compound

Product 1

HCID 69244216HCID 69244216, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 9,10-dihydro anthracene-1,5-dicarboxylic acid (52, 1 g, 3.73 mmol) in 200 μl of dimethyl formamide and 20 ml of thionyl chloride was refluxed for 3 hours. The resulting solution was evaporated to dryness under vacuum, 60 ml of benzene added, and warmed to 60° C. to obtain a solution. This solution was slowly added to a 250 ml round bottom flask containing a mixture of AlCl3 and 20 ml of benzene. The resulting mixture was stirred for 18 hours at room temperature and poured into 100 ml of an ice/water mixture containing 10 ml of conc. HCl. The organic layer was separated and the aqueous layer was washed twice with 100 ml portions of benzene. After drying over Na2SO4, the combined organic extracts were dried under vacuum to yield a brown colored crude product. This was further purified by flash column chromatography to obtain a dark yellow, oily product (0.39 g, 27%) (According to NMR studies the product is 80+% pure). 1H NMR (300 MHz, CDCl3): δ 4.04 (s, 4H), 7.20-7.86 (m, 16H), 7.51 (d, 2H, J=6 Hz), 7.70 (d, 2H, J=6 Hz), 13.00 (broad s, 2H). 13C NMR (300 MHz, CDCl3): δ 33.95, 125.48, 126.98, 128.51, 128.55, 129.94, 130.30, 133.24, 135.74, 137.88, 197.15.

Workup

  1. customThe resulting solution was evaporated to dryness under vacuum, 60 ml of benzene
  2. additionadded
  3. customto obtain a solution
  4. additionThis solution was slowly added to a 250 ml round bottom flask
  5. additioncontaining
  6. customThe organic layer was separated
  7. washthe aqueous layer was washed twice with 100 ml portions of benzene
  8. dry with materialAfter drying over Na2SO4
  9. customthe combined organic extracts were dried under vacuum
  10. customto yield a brown colored crude product
  11. customThis was further purified by flash column chromatography

Sources & evidence

ORD record
ord-33baa667be71499b83dcb070d6ea8aca
Source dataset
uspto-grants-2012_08
Patent number
US08242162B2

Reaction notes

Loading…