Heptylbenzene → HCID 22420397, compound

HRID 1720159Notes

Reaction equation

HRID 1720159 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:8][C:7](=[O:9])[O:6][C:4](=[O:5])[CH2:3]1.[C:11]1([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl-].[Al+3].[Cl-].[Cl-]>Cl>[CH2:17]([C:11]1[CH:12]=[CH:13][C:14]([C:7]([CH2:8][C:2]([CH3:1])([CH3:10])[CH2:3][C:4]([OH:6])=[O:5])=[O:9])=[CH:15][CH:16]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 14115HeptylbenzeneHCID 778133,3-Dimethylglutaric anhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 22420397HCID 22420397, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

First, 3,3-dimethylglutaric anhydride (25 g, 0.176 moles) is heated with 1-phenylheptane (150 ml) and anhydrous aluminium chloride (51.6 g, 0.387 moles) at 90°-100° C. for 1 hour. The reaction mixture is cooled to room temperature, poured into a mixture of ice water (500 ml) and concentrated hydrochloric acid (100 ml), and extracted with ether (3×150). The combined ether extracts are dried over anhydrous magnesium sulfate and filtered. Ether is removed under reduced pressure and the resulting solution chromatographed on silica gel (hexane and then hexane:ether:acetic acid at 80:20:1) to yield 4-(4-heptylbenzoyl)-3,3-dimethyl butanoic acid (17.67 g), m.p. 41°-42° C.

Workup

  1. extractionextracted with ether (3×150)
  2. dry with materialThe combined ether extracts are dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customEther is removed under reduced pressure
  5. customthe resulting solution chromatographed on silica gel (hexane

Sources & evidence

ORD record
ord-2eba59ebe0994f20afb048343cf00026
Source dataset
uspto-grants-1996_04
Patent number
US05504244

Reaction notes

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