Hydrochloric Acid → HCID 54295527, compound

HRID 1590449Notes

Reaction equation

HRID 1590449 reaction equation
[CH3:1][C:2]([CH3:16])=[CH:3][CH2:4][CH2:5]/[C:6](/[CH3:15])=[CH:7]/[CH2:8][CH2:9]/[C:10](/[CH3:14])=[CH:11]/[CH2:12][OH:13].[C:17]([O:21]C)(=[O:20])[CH:18]=[CH2:19].CC(C)([O-])C.[K+].O1CCCC1.C(O)(C)(C)C.Cl>>[CH2:12]([O:13][CH2:19][CH2:18][C:17]([OH:21])=[O:20])[CH:11]=[C:10]([CH2:9][CH2:8][CH:7]=[C:6]([CH2:5][CH2:4][CH:3]=[C:2]([CH3:16])[CH3:1])[CH3:15])[CH3:14]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7294Methyl AcrylateHCID 445070FarnesolHCID 131717860HCID 131717860, compound

Product 1

HCID 54295527HCID 54295527, compound

Procedure

All-trans-farnesol was reacted with methyl acrylate in the presence of one equivalent of 0.1 equivalent of potassium-tert butoxide/tetrahydorfuran/t-butanol for three hours at room temperature. The solution was acidified with 0.1N HCl, evaporated to dryness, and purified by thin layer chromatography on silica. The free acid was prepared by treatment of the ester with potassium hydroxide in methanol. The product showed the anticipated nmr and infrared spectra.

Workup

  1. customevaporated to dryness
  2. custompurified by thin layer chromatography on silica
  3. customThe free acid was prepared by treatment of the ester with potassium hydroxide in methanol

Sources & evidence

ORD record
ord-a36ee802dfb049cc80a97c6258617d35
Source dataset
uspto-grants-1993_04
Patent number
US05202456

Reaction notes

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