Toluene → rac-(2RS,3RS,5SR)-3-benzoyloxy-2-hexyl-5-undecyl-delta-valerolactone

HRID 1609352Notes

Reaction equation

HRID 1609352 reaction equation
[C:1]([O:9][C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl(O)(=O)(=O)=O.[C:23]1([CH3:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[C:10]([O:9][CH:1]1[CH2:2][CH:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[O:17][C:10](=[O:9])[CH:24]1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:23][CH3:29])(=[O:17])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 7167Benzoic anhydrideHCID 24247Perchloric Acid

Product 1

HCID 22463416rac-(2RS,3RS,5SR)-3-benzoyloxy-2-hexyl-5-undecyl-delta-valerolactoneYield 103.4%

Procedure

177.3 g of the δ-lactone from c) were suspended in 1250 ml of toluene while stirring. After the addition of 138.6 g of benzoic anhydride the mixture was stirred for 10 minutes. Then, 2.5 ml of perchloric acid were added. The mixture was stirred for a further 2.5 hours. The reaction solution was extracted in toluene with 1N sodium hydroxide solution and then with water. The combined toluene phases were dried, the drying agent was filtered off under suction and washed with toluene. Evaporation of the solvent gave 237.2 g (103.4%) of rac-(2RS,3RS,5SR)-3-benzoyloxy-2-hexyl-5-undecyl-δ-valerolactone, which was used in the next step without purification.

Workup

  1. stirringwas stirred for 10 minutes
  2. stirringThe mixture was stirred for a further 2.5 hours
  3. extractionThe reaction solution was extracted in toluene with 1N sodium hydroxide solution
  4. dry with materialThe combined toluene phases were dried
  5. filtrationthe drying agent was filtered off under suction
  6. washwashed with toluene
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-272bceb7bdb94b6cbe916a1a9d71db5f
Source dataset
uspto-grants-1995_03
Patent number
US05399720

Reaction notes

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