Toluene → rac-(2RS,3RS,5SR)-3-benzoyloxy-2-ethyl-5-heptadecyl-delta-valerolactone

HRID 5625

Reaction equation

HRID 5625 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][CH2:5][CH2:4][CH2:3][CH2:2][CH2:7][CH2:6][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:23][CH3:29])[O:17][C:10](=[O:9])[CH:11]1[CH2:12][CH3:13])(=[O:17])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 3

HCID 1140Toluene2×HCID 7167Benzoic anhydrideHCID 24247Perchloric Acid

Product 1

HCID 67808146rac-(2RS,3RS,5SR)-3-benzoyloxy-2-ethyl-5-heptadecyl-delta-valerolactoneYield 100%

Procedure

138.5 g of benzoic anhydride and subsequently 2.5 ml of perchloric acid 70% were added to a suspension of 191.3 g of the δ-lactone from c) in 1250 ml of toluene. After stirring for 2.5 hours the reaction mixture in toluene was extracted with 1N sodium hydroxide solution in 20% sodium chloride solution and then with saturated sodium chloride solution. The organic phases were combined, dried and evaporated. 243.4 g (100.0%) of rac-(2RS,3RS,5SR)-3-benzoyloxy-2-ethyl-5-heptadecyl-δ-valerolactone, m.p. 64.5°-66°, resulted.

Workup

  1. extractionwas extracted with 1N sodium hydroxide solution in 20% sodium chloride solution
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-2e4259a4f0b9499a99678dde8cd38979
Source dataset
uspto-grants-1993_09
Patent number
US05245056

Linked notes

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