O-Xylene → HCID 21416084, compound

HRID 1729777Notes

Reaction equation

HRID 1729777 reaction equation
O[CH:2]([CH2:10][CH2:11][CH2:12][CH2:13]C)[CH2:3][CH2:4][CH2:5][C:6](=[O:9])C=C.CC1C(=[O:21])CCC1=O.C1(C)C(C)=CC=CC=1>C(O)(=O)C>[O:9]1[C:13]2[CH2:12][C:11](=[O:21])[CH:10]=[CH:2][C:3]=2[CH:4]=[CH:5][CH2:6]1

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 130052-Methyl-1,3-cyclopentanedioneHCID 21501121HCID 21501121, compound

Product 1

HCID 21416084HCID 21416084, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of the optically active 7-hydroxy-1-dodecen-3-one, obtained as described in Example 4, 2.25 grams of 2-methylcyclopentane-1,3-dione, 50 milliliters of xylene, and 25 milliliters of acetic acid was refluxed for 11/2 hours under a nitrogen atmosphere. After evaporation under vacuum, the residue was extracted with cold benzene leaving 400 milliliters of unreacted methylcyclopentanedione as an insoluble residue. The benzene solution was then evaporated to yield 5.56 grams of optically active 3-pentyl-6aβ-methyl-1,2,3,5,6,6a-hexahydrocyclopenta]f][1]benzopyran-7(8H)-one. After chromatographing the crude product on alumina, followed by crystallization from methanol-water, the product melted at 60°-61°C., [α]D25 -166°.

Workup

  1. customobtained
  2. temperaturewas refluxed for 11/2 hours under a nitrogen atmosphere
  3. customAfter evaporation under vacuum
  4. extractionthe residue was extracted with cold benzene leaving 400 milliliters of unreacted methylcyclopentanedione as an insoluble residue
  5. customThe benzene solution was then evaporated

Sources & evidence

ORD record
ord-7f8f5004ca4c4ae6a49a6a872561dc80
Source dataset
uspto-grants-1976_11
Patent number
US03989724

Reaction notes

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