Hydrochloric Acid → 3-[9-methoxy-5,9-dimethyl-2(E)decenoyl]-4-butyrolactone

HRID 67126Notes

Reaction equation

HRID 67126 reaction equation
Cl.[CH3:2][O:3][C:4]([CH3:23])([CH3:22])[CH2:5][CH2:6][CH2:7][CH:8]([CH3:21])[CH2:9][CH:10](O)[CH2:11][C:12]([CH:14]1[CH2:19][O:18][C:16](=[O:17])[CH2:15]1)=[O:13].O>CO>[CH3:2][O:3][C:4]([CH3:22])([CH3:23])[CH2:5][CH2:6][CH2:7][CH:8]([CH3:21])[CH2:9]/[CH:10]=[CH:11]/[C:12]([CH:14]1[CH2:19][O:18][C:16](=[O:17])[CH2:15]1)=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 20528523HCID 20528523, compound

Product 1

HCID 205285203-[9-methoxy-5,9-dimethyl-2(E)decenoyl]-4-butyrolactoneYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1 ml of methanol saturated with hydrochloric acid is added to a solution of 2.1 g (0.007 moles) of 3-(9-methoxy-3-hydroxy-5,9-dimethyl-decanoyl)-4-butyrolactone in 15 ml of dry methanol, and the mixture is allowed to stand at room temperature for 12 hours. 2 ml of water are added to the mixture, and the mixture is stirred at room temperature for 5 hours. The solvent is distilled off in vacuo, the residue is taken up in ether, the etheral solution is washed with water, dried, and the solvent is distilled off. The residue is purified by chromatography (adsorbent: Kieselgel 60, solvent: a 10:0.1 mixture of benzene and methanol). 1.4 g (70%) of the aimed compound are obtained; Rf =0.75 (developed with a 10:0.1 mixture of benzene and methanol).

Workup

  1. distillationThe solvent is distilled off in vacuo
  2. washthe etheral solution is washed with water
  3. customdried
  4. distillationthe solvent is distilled off
  5. customThe residue is purified by chromatography (adsorbent
  6. additionKieselgel 60, solvent: a 10:0.1 mixture of benzene and methanol)

Sources & evidence

ORD record
ord-e34b4949855945b3af8d302e25c3a41e
Source dataset
uspto-grants-1982_08
Patent number
US04344959

Reaction notes

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