Water → HCID 10634975, compound

HRID 1637571Notes

Reaction equation

HRID 1637571 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][S:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17].[OH-].[K+].C[O-].[K+].O>OCC(CO)O>[C:16]1(=[O:17])[O:18][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][S:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 11140370HCID 11140370, compoundHCID 23664618Potassium methoxide2×

Product 1

HCID 10634975HCID 10634975, compound

Reagents, catalysts & solvents 1

HCID 753GlycerolSolvent2×

Conditions

Temperature
153 °C

Procedure

22 g of crude 15-hydroxy-7-thiapentadecanoic acid (9, n=3, m=7, R=H) was treated with 0.45 ml (4.0 mmol) of 50 percent potassium hydroxide solution and byproducts were distilled off at 180° C./20-23 mbar for 1 h. Thereupon, the reaction vessel was fitted with a condenser and separator and 1.2 g (17 mmol) of potassium methylate in 300 ml of anhydrous glycerol was added to the reaction mixture. The mixture was heated to reflux at 153° C./4-6 mbar over the separator for 2 d., with 1.2 g (17 mmol) of potassium methylate again being added after 14 h. The separated glycerol was poured into 800 ml of water and the crude product was extracted twice with 500 ml of MTBE each time and once with 500 ml of n-pentane. The combined organic extracts were dried over magnesium sulphate and concentrated to dryness on a rotary evaporator. After flash chromatography (n-pentane/MTBE, 19:1, hRf=46) on silica gel, 2.9 g (11% overall yield) of 7-thia-pentadecanolide as a colorless wax-like solid with an intensive, linear musk odor accompanied by green-mossy aspects with a threshold value of 0.2 ng/l air was obtained.

Workup

  1. distillationwere distilled off at 180° C./20-23 mbar for 1 h
  2. customThereupon, the reaction vessel was fitted with a condenser
  3. temperatureThe mixture was heated
  4. extractionthe crude product was extracted twice with 500 ml of MTBE each time
  5. dry with materialThe combined organic extracts were dried over magnesium sulphate
  6. concentrationconcentrated to dryness on a rotary evaporator
  7. customwas obtained

Sources & evidence

ORD record
ord-5d045378b972457d9af60926cd975609
Source dataset
uspto-grants-2000_03
Patent number
US06043210

Reaction notes

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