Sulfuric Acid → HCID 9859453, compound

HRID 1756715Notes

Reaction equation

HRID 1756715 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([OH:9])=[O:8].S(=O)(=O)(O)O.[C:15](=[O:18])(O)[O-].[Na+]>CO>[O:1]1[C:15](=[O:18])[CH2:6][O:5][CH2:4][CH2:3][CH2:2][O:8][C:7](=[O:9])[CH2:6][O:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 22500968HCID 22500968, compound

Product 1

HCID 9859453HCID 9859453, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

271.2 Grams (2.02 moles) of crude 6-hydroxy-3-oxa-caproic acid, as prepared in Example 1, 3.5 liters (87 moles) of reagent grade methanol, and 0.2 grams (2 mmol) of concentrated sulfuric acid were charged into a five liter, round bottom flask containing some boiling chips. A reflux condenser connected to a dry stream of nitrogen gas via tubing was attached, and the solution was heated to reflux with an oil bath for twenty four hours. After the solution had cooled down, 5.00 grams (59.5 mmol) of sodium bicarbonate were added, and a distillation head was attached. The methanol was distilled off at atmospheric pressure. After the methanol was removed, the orangish brown residue was vacuum filtered into a tared, one liter round bottom flask containing a magnetic stirring bar. 297 grams of crude methyl 6-hydroxy-3-oxa-caproate were collected (99.0% yield). A still head was attached, and the crude product was vacuum distilled. Initially, a colorless liquid distilled over between 88° C. and 90° C. (0.01 mm Hg), but the distillation rate eventually slowed down. After two hours, some crystals of 1,5,8,12-tetraoxacyclotetradecane-7,14-dione formed in the condenser. The distillation was stopped. The collection flask was placed in the refrigerator overnight. Crystals of 1,5,8,12-tetraoxacyclotetradecane-7,14-dione formed in the collection flask and were removed by suction filtration. These crystals were washed with 100 mL of ethyl acetate and air dried. 4.11 grams of 1,5,8,12-tetraoxacyclotetradecane-7,14-dione and 67.5 grams of supernatent liquid A were isolated.

Workup

  1. additionwere charged into a five liter, round bottom flask
  2. additioncontaining some boiling chips
  3. customA reflux condenser connected to a dry stream of nitrogen gas
  4. temperaturethe solution was heated
  5. temperatureto reflux with an oil bath for twenty four hours
  6. temperatureAfter the solution had cooled down
  7. distillationThe methanol was distilled off at atmospheric pressure
  8. customAfter the methanol was removed
  9. filtrationfiltered into
  10. additionone liter round bottom flask containing a magnetic stirring bar
  11. custom297 grams of crude methyl 6-hydroxy-3-oxa-caproate were collected (99.0% yield)
  12. distillationdistilled
  13. distillationInitially, a colorless liquid distilled over between 88° C. and 90° C. (0.01 mm Hg)

Sources & evidence

ORD record
ord-f269496a69ce439a8d7b9a50e409a1a2
Source dataset
uspto-grants-1995_08
Patent number
US05442032

Reaction notes

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