Hydrochloric Acid → HCID 19862973, compound

HRID 845730Notes

Reaction equation

HRID 845730 reaction equation
[C:1]([CH2:11][C:12]1([CH:18]([C:20]([O:22]C)=[O:21])[CH3:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[OH-].[Na+].Cl>O1CCOCC1>[C:1]([CH2:11][C:12]1([CH:18]([C:20]([OH:22])=[O:21])[CH3:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19862974HCID 19862974, compound

Product 1

HCID 19862973HCID 19862973, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the above 1-carbobenzoxymethyl-1-carbomethoxyethylcyclohexane (40.4 g) in dioxane (300 ml) was added 1N NaOH (150 ml) dropwise over 2 hours with stirring at room temperature. After 6 hours the reaction was neutralized with 1N HCl then the dioxane was evaporated. The cloudy solution was diluted with water, acidified with 1N HCl, then extracted two times with ethyl acetate, washed with saturated NaCl (aqueous), dried with MgSO4, filtered and then concentrated to an oil. By 1H-NMR no mono methyl ester could be seen in the crude reaction mixture, the major by-product being the di acid. The product was purified by flash chromatography (silica gel, eluted with CHCl3, MeOH,HOAc 99:1:0.1) then distilled free of the residual benzyl alcohol to give 1-carbobenzoxymethyl-1-carboxyethylcyclohexane. (29.6 g, 76%) 1H-NMR. (CDCl3) δ7.05(s,5H); 4.9(s,2H); 2.35-2.1(m,2H); 2.2(s,2H); 1.85-1.55(m,2H); 1.35(br s,10H).

Workup

  1. customthe dioxane was evaporated
  2. additionThe cloudy solution was diluted with water
  3. extractionextracted two times with ethyl acetate
  4. washwashed with saturated NaCl (aqueous)
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to an oil
  8. customreaction mixture
  9. customThe product was purified by flash chromatography (silica gel, eluted with CHCl3, MeOH,HOAc 99:1:0.1)
  10. distillationthen distilled free of the residual benzyl alcohol

Sources & evidence

ORD record
ord-a651b5b893fa4bbf84fe017f89bcc97f
Source dataset
uspto-grants-1988_07
Patent number
US04760052

Reaction notes

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