Hydrochloric Acid → HCID 53940607, compound

HRID 1288090Notes

Reaction equation

HRID 1288090 reaction equation
[C:1]([CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][C:12]1(C(OCC)=O)[C@H:16](/[CH:17]=[CH:18]/[C:19]([OH:26])([CH3:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:15][C@H:14](C(OCC)=O)[C:13]1=[O:32])([O:3]CC)=[O:2].[OH-].[Na+].Cl>O.CO.[Cl-].[Na+]>[OH:26][C:19]([CH3:25])([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:18]=[CH:17][C@H:16]1[CH2:15][CH2:14][C:13](=[O:32])[C@H:12]1[CH2:11][CH:10]=[CH:9][CH2:8][CH2:7][CH2:6][C:1]([OH:3])=[O:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86734085HCID 86734085, compound

Product 1

HCID 53940607HCID 53940607, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 5234Sodium ChlorideSolvent

Procedure

The cyclopentanonetriester of formula 6, diethyl cis,-trans-3-(6-carboethoxy-2-hexenyl)-4-(3-hydroxy-3-methyl-1-octenyl)-2-oxo-1,3-cyclopentanedicarboxylate (11.2 g), described in Example 45, is heated to reflux for 1 hr. in a solution of sodium hydroxide (13.4 g) in 80 ml of water and 110 ml of methanol. The mixture is cooled, adjusted to pH 5 with 2N HCl, diluted with saturated sodium chloride solution and extracted with ether. The ether extract is dried (Na2SO4) and concentrated. Chromatography on silica gel yields the title compound νmax CHCl 3 3580, 1740, 1720 cm-1, nmr (CDCl3) δ 0.88 (t, J = 5, 3H), 1.28 (s, 3H), 5.3 - 5.75 (m, 4H), 6.3 (2xs, 2H).

Workup

  1. temperatureis heated
  2. temperatureto reflux for 1 hr
  3. temperatureThe mixture is cooled
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. dry with materialis dried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9c2942fac8914897862caec6b1c91c96
Source dataset
uspto-grants-1976_10
Patent number
US03987081

Reaction notes

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