Hydrochloric Acid → HCID 22420399, compound

HRID 1720172Notes

Reaction equation

HRID 1720172 reaction equation
[C:1]1(=[O:8])[O:7][C:5](=[O:6])[CH2:4][CH2:3][CH2:2]1.[C:9]1([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>O>[CH2:15]([C:9]1[CH:10]=[CH:11][C:12]([C:5]([CH2:4][CH2:3][CH2:2][C:1]([OH:7])=[O:8])=[O:6])=[CH:13][CH:14]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7940Glutaric anhydrideHCID 14115HeptylbenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 22420399HCID 22420399, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Glutaric anhydride (77.6 g) is added in one portion to a stirred mixture of 1-phenylheptane (400 ml) and anhydrous aluminum chloride (200 g). The mixture is stirred at room temperature for 1 hour, then cooled in an ice bath and carefully treated with a mixture of water (300 ml) and conc. HCl (100 ml). After the addition is complete, the mixture is allowed to return to room temperature and then extracted with ether (3×500 ml). The combined ether extracts are dried over MgSO4, filtered and concentrated on a rotary evaporator. The solid precipitate is separated from the phenyl heptane solution, and then mixed with water (600 ml) and heated under reflux for 15 min. After cooling to room temperature the product is extracted with methylene chloride (2×300 ml). The extract is dried over MgSO4, filtered and concentrated. The residue is recrystallized from heptane to provide 4-(4-n-heptylbenzoyl)butanoic acid (34.86 g) as a white crystalline solid, m.p. 101°-103.5°0 C.

Workup

  1. temperaturecooled in an ice bath
  2. additionAfter the addition
  3. customto return to room temperature
  4. extractionextracted with ether (3×500 ml)
  5. dry with materialThe combined ether extracts are dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated on a rotary evaporator
  8. customThe solid precipitate is separated from the phenyl heptane solution
  9. additionmixed with water (600 ml)
  10. temperatureheated
  11. temperatureunder reflux for 15 min
  12. temperatureAfter cooling to room temperature the product
  13. extractionis extracted with methylene chloride (2×300 ml)
  14. dry with materialThe extract is dried over MgSO4
  15. filtrationfiltered
  16. concentrationconcentrated
  17. customThe residue is recrystallized from heptane

Sources & evidence

ORD record
ord-b9e1308aa98e4be89bea6c7c3742def5
Source dataset
uspto-grants-1996_04
Patent number
US05504244

Reaction notes

Loading…