Heptylbenzene → HCID 54486030, compound

HRID 1720158Notes

Reaction equation

HRID 1720158 reaction equation
[C@@H:1]12[C:10](=[O:11])[O:9][C:7](=[O:8])[C@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6]2.[C:12]1([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl-].[Al+3].[Cl-].[Cl-]>Cl>[CH2:18]([C:12]1[CH:13]=[CH:14][C:15]([C:7]([C@@H:2]2[CH2:3][CH2:4][CH2:5][CH2:6][C@H:1]2[C:10]([OH:9])=[O:11])=[O:8])=[CH:16][CH:17]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 14115HeptylbenzeneHCID 6451240Aluminum(III) ChlorideHCID 12261141(-)-trans-1,2-Cyclohexanedicarboxylic Anhydride

Product 1

HCID 54486030HCID 54486030, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Trans-1,2-cyclohexanedicarboxylic anhydride (6.76 g , 0.044 mole) was heated with 1-phenylheptane (100 ml) and anhydrous aluminum chloride (12.86 g, 0.096 moles) at 100° C. for 1 hour. The reaction mixture was then poured into a mixture of ice water (500 ml) and concentrated hydrochloric acid (50 ml). The product was extracted with ether (2×200 ml) and the extracts dried over magnesium sulfate and filtered. The ether was removed under reduced pressure and the remaining solution chromatographed on silica (hexane and then hexane:ether:acetic acid at 70:30:1) to yield trans-2-(4-heptylbenzoyl) cyclohexane-1-carboxylic acid (7.36 g), m.p. 91°-94° C.

Workup

  1. extractionThe product was extracted with ether (2×200 ml)
  2. dry with materialthe extracts dried over magnesium sulfate
  3. filtrationfiltered
  4. customThe ether was removed under reduced pressure
  5. customthe remaining solution chromatographed on silica (hexane

Sources & evidence

ORD record
ord-ad93d9dc0d734e5586042c28a254a0f3
Source dataset
uspto-grants-1996_04
Patent number
US05504244

Reaction notes

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