Sodium Hydroxide → HCID 178525777, compound

HRID 237329Notes

Reaction equation

HRID 237329 reaction equation
C([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([O:12][CH:13]([CH2:26][OH:27])[CH2:14]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:8][CH2:7]1)=[O:5])C.CC(C)([O-])C.[K+].[OH-].[Na+]>C1(C)C=CC=CC=1>[O:27]1[CH2:14][CH:13]([O:12][C@H:9]2[CH2:8][CH2:7][C@H:6]([C:4]([OH:3])=[O:5])[CH2:11][CH2:10]2)[CH2:26]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 23665647Potassium tert-butoxideHCID 178472496HCID 178472496, compound

Product 1

HCID 178525777HCID 178525777, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of cis/trans-4-[1-hydroxymethyl-2-(toluene-4-sulfonyloxy)-ethoxy]-cyclohexanecarboxylic acid ethyl ester (3:7) (0.46 g, 1.2 mmol) in toluene (11.5 ml) was added potassium tert-butoxide (0.14 g, 1.3 mmol). The reaction mixture was heated at reflux for 20 h. After cooling to room temperature the mixture was partitioned between ethyl acetate (50 ml) and 1 M aqueous hydrogen chloride solution (30 ml). The layers were separated. The aqueous layer was extracted with two 50-ml portions of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was dissolved in 1,4-dioxane (12 ml) and 2 M aqueous sodium hydroxide solution (5.7 ml, 12 mmol). After stirring at room temperature for 16 h the mixture was partitioned between tert-butyl methyl ether (30 ml) and 1 M aqueous sodium hydroxide solution (50 ml). The layers were separated. The organic layer was extracted with one 50-ml portion of 1 M aqueous sodium hydroxide solution. The combined aqueous layers were acidified by addition of concentrated hydrochloric acid solution and crushed ice (50 g) and extracted with three 50-ml portions of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. Flash-chromatography with n-heptane/ethyl acetate as eluent gave the title compound (0.12 g, 50%) as off-white solid. MS m/e: 199 (M+H+)

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 20 h
  3. customwas partitioned between ethyl acetate (50 ml) and 1 M aqueous hydrogen chloride solution (30 ml)
  4. customThe layers were separated
  5. extractionThe aqueous layer was extracted with two 50-ml portions of ethyl acetate
  6. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residue was dissolved in 1,4-dioxane (12 ml)
  9. customwas partitioned between tert-butyl methyl ether (30 ml) and 1 M aqueous sodium hydroxide solution (50 ml)
  10. customThe layers were separated
  11. extractionThe organic layer was extracted with one 50-ml portion of 1 M aqueous sodium hydroxide solution
  12. additionThe combined aqueous layers were acidified by addition of concentrated hydrochloric acid solution
  13. customcrushed ice (50 g)
  14. extractionextracted with three 50-ml portions of ethyl acetate
  15. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  16. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-808379400b364f559c8d5a8b89a6f75d
Source dataset
uspto-grants-2014_02
Patent number
US08642590B2

Reaction notes

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