Acetic Acid → HCID 58915394, compound

HRID 1297531Notes

Reaction equation

HRID 1297531 reaction equation
[N+:1]([O-:4])(O)=[O:2].CC(O)=O.[CH3:9][C:10]([CH3:21])([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:11]=[CH2:12]>CC(OC(C)=O)=O>[CH3:9][C:10]([CH3:21])([CH:11]=[CH2:12])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:1]([O-:4])=[O:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 568706Benzene, (3,3-dimethyl-4-pentenyl)-

Product 1

HCID 58915394HCID 58915394, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent2×

Procedure

In a flask, was loaded fuming HNO3 (18.7 mL, 90%, d=1.5), HOAc (18 mL), Ac2O (14 mL), which was allowed to cool back to room temperature before proceeding. This solution was added dropwise to 3,3-dimethyl-5-phenyl-1-pentene (45.8 g, 0.263 mol), which was prepared using the procedure of Reike and coworkers referenced as 12 in the manuscript, in Ac2O (120 mL). The reaction was kept between 0 and −5° C. during the addition. After the addition, the mixture was stirred at 0° C. for 12 h. The reaction mixture was poured into crushed ice (300 g) The product was extracted with ethyl ether (3×200 mL) and the combined organic layers were washed with portions of saturated NaHCO3 (˜300 mL total) until no gas formed on addition of the basic aqueous solution. The organic solution was filtered, and the separated solids were washed with ether (50 mL). The combined aqueous layers were extracted with ether (3×200 mL). The combined ether solutions were dried with MgSO4. The volatiles were removed in vacuo providing the product as a yellow oil in 97% yield (55.95 g) as a mixture of isomers. GC/FID analysis displayed an ortho:para ratio of 49:51. The compound was used without further purification.

Workup

  1. customIn a flask, was loaded fuming
  2. customwas prepared
  3. additionThe reaction was kept between 0 and −5° C. during the addition
  4. additionAfter the addition
  5. additionThe reaction mixture was poured
  6. extractionwas extracted with ethyl ether (3×200 mL)
  7. washthe combined organic layers were washed with portions of saturated NaHCO3 (˜300 mL total) until no gas
  8. customformed on addition of the basic aqueous solution
  9. filtrationThe organic solution was filtered
  10. washthe separated solids were washed with ether (50 mL)
  11. extractionThe combined aqueous layers were extracted with ether (3×200 mL)
  12. dry with materialThe combined ether solutions were dried with MgSO4
  13. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-df8ed08571ff48b6be2aaf3ab0413b8a
Source dataset
uspto-grants-2007_07
Patent number
US07250523B2

Reaction notes

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