Potassium Hydroxide → HCID 11140370, compound

HRID 1637570Notes

Reaction equation

HRID 1637570 reaction equation
CN(C)[C:3](=[S:7])N(C)C.IC[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17]CC)=[O:16].[CH2:20](O)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28].[H-].[Na+].[OH-].[K+]>C(#N)C.CC(OC)(C)C.CCCCC>[OH:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][S:7][CH2:3][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16]

Participants

8

Reactant 5

HCID 14797Potassium HydroxideHCID 177251,1,3,3-Tetramethyl-2-thioureaHCID 24758Sodium hydrideHCID 694201,8-OctanediolHCID 10880140Ethyl 6-iodohexanoate

Product 1

HCID 11140370HCID 11140370, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 22145886HCID 22145886, compoundSolvent

Conditions

Temperature
50 °C

Procedure

a solution of 14 g (0.11 mol) of tetramethylthiourea and 28 g (0.10 mol) of ethyl 6-iodocaproate in 220 ml of dry acetonitrile was heated under reflux for 2 h. In a further reaction vessel 23 g (0.16 mol) of 1,8-octanediol was dissolved in 650 ml of dry acetonitrile under argon, the solution was treated with 4.5 g (0.11 mol) of a 60 percent sodium hydride suspension in mineral oil and heated under reflux for 45 min. Both batches were left to cool to 50° C. and thereupon combined cautiously within 30 min. The combined reaction mixtures were heated to reflux for 14 h., subsequently saponified with 60 ml of 10 percent potassium hydroxide solution for 3 h. at room temp., concentrated on a rotary evaporator and then added to 1 l of water. The mixture was extracted twice with 500 ml of MTBE each time, and the organic extracts were washed three times with 50 ml of 2N sodium hydroxide solution each time. The aqueous phase was acidified with conc. phosphoric acid and extracted three times with 500 ml of MTBE each time. After drying the combined organic extracts over magnesium sulphate and removing the solvent on a rotary evaporator 22 g of crude 15-hydroxy-7-thiapentadecanoic acid as a yellowish wax-like solid was obtained. An analytical sample was obtained after flash chromotography (MTBE/n-pentane, 2:1, hRf =33) on silica gel.

Workup

  1. temperatureunder reflux for 2 h
  2. temperatureheated
  3. temperatureunder reflux for 45 min
  4. waitBoth batches were left
  5. customThe combined reaction mixtures
  6. temperaturewere heated
  7. temperatureto reflux for 14 h.
  8. concentrationconcentrated on a rotary evaporator
  9. additionadded to 1 l of water
  10. extractionThe mixture was extracted twice with 500 ml of MTBE each time
  11. washthe organic extracts were washed three times with 50 ml of 2N sodium hydroxide solution each time
  12. extractionextracted three times with 500 ml of MTBE each time
  13. dry with materialAfter drying the combined organic extracts over magnesium sulphate
  14. customremoving the solvent
  15. customon a rotary evaporator 22 g of crude 15-hydroxy-7-thiapentadecanoic acid as a yellowish wax-like solid
  16. customwas obtained

Sources & evidence

ORD record
ord-42a544d7e86b44cd874b0431baffcea9
Source dataset
uspto-grants-2000_03
Patent number
US06043210

Reaction notes

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