Hydrochloric Acid → 3-[1,9-dimethoxy-5,9-dimethyl-2(E)decenylidene]-4-butyrolactone

HRID 67125Notes

Reaction equation

HRID 67125 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].[CH3:24]O>>[CH3:24][O:13][C:12](=[C:14]1[CH2:19][O:18][C:16](=[O:17])[CH2:15]1)/[CH:11]=[CH:10]/[CH2:9][CH:8]([CH3:21])[CH2:7][CH2:6][CH2:5][C:4]([O:3][CH3:2])([CH3:23])[CH3:22]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 20528523HCID 20528523, compound

Product 1

HCID 867385323-[1,9-dimethoxy-5,9-dimethyl-2(E)decenylidene]-4-butyrolactoneYield 52.1%

Procedure

1 ml of methanol saturated with hydrochloric acid is added to a solution of 1.05 g (0.0033 moles) of 3-(9-methoxy-3-hydroxy-5,9-dimethyl-decanoyl)-4-butyrolactone in 10 ml of dry methanol, and the mixture is allowed to stand at room temperature overnight. The solvent is distilled off in vacuo, the residue is dissolved in ether, the etheral solution is washed with distilled water, dried, the solvent is distilled off, and the residue is purified by column chromatography (adsorbent: Kieselgel 60, solvent: a 10:0.1 mixture of benzene and methanol). 0.54 g (52.1%) of the aimed compound are obtained; Rf =0.8 (developed with a 10:0.2 mixture of benzene and methanol).

Workup

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

Sources & evidence

ORD record
ord-71a010aa3742498d8fbca5124bc9b087
Source dataset
uspto-grants-1982_08
Patent number
US04344959

Reaction notes

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