HCID 15044953, compound → HCID 15044954, compound

HRID 728058Notes

Reaction equation

HRID 728058 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]([CH2:17][CH2:18][CH:19]([C:23]2[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH3:32])=[C:25]([O:33][CH3:34])[CH:24]=2)C(O)=O)[C:14](O)=[O:15])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]>C(OC(=O)C)(=O)C>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C@H:13]2[CH2:17][CH2:18][C@H:19]([C:23]3[CH:24]=[C:25]([O:33][CH3:34])[C:26]([O:31][CH3:32])=[C:27]([O:29][CH3:30])[CH:28]=3)[C:14]2=[O:15])[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]

Participants

3

Reactant 1

HCID 15044953HCID 15044953, compound

Product 1

HCID 15044954HCID 15044954, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of α,α'-bis(3,4,5-trimethoxyphenyl)adipic acid (10 g, 21 mmoles) and acetic anhydride (30 ml) was heated at 150° C. for 30 minutes. Acetic acid and anhydride were removed in vacuo. The flask containing the solid residue was fitted with a distillation head and while under vacuum (~150 mm) was placed in an oil bath heated to 287° C. The solid melted; there was a vigorous evolution of gas and about 5 ml of liquid distilled. After 6.5 minutes the flask was cooled rapidly with a water bath. The yellow-brown syrupy residue was dissolved in 80 ml of hot ethanol, filtered from some insoluble material and seeded. After standing at room temperature overnight, the crystalline solid was filtered, washed with cold ethanol (3 times) and dried to give 5.57 g (64%) of trans-2,5-bis(3,4,5-trimethoxyphenyl)cyclopentanone, m.p. 140°-142.5°. IR 174 cm-1 (C=O), mass spec m/e 416 (M+).

Workup

  1. customAcetic acid and anhydride were removed in vacuo
  2. additionThe flask containing the solid residue
  3. customwas fitted with a distillation head and while under vacuum (~150 mm)
  4. customwas placed in an oil bath
  5. temperatureheated to 287° C
  6. distillationdistilled
  7. temperatureAfter 6.5 minutes the flask was cooled rapidly with a water bath
  8. dissolutionThe yellow-brown syrupy residue was dissolved in 80 ml of hot ethanol
  9. filtrationfiltered from some insoluble material
  10. filtrationthe crystalline solid was filtered
  11. washwashed with cold ethanol (3 times)
  12. customdried

Sources & evidence

ORD record
ord-719936848ec74dd49136a9057dcd53d7
Source dataset
uspto-grants-1991_09
Patent number
US05047420

Reaction notes

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