Sulfuric Acid → HCID 91119464, compound

HRID 1744776Notes

Reaction equation

HRID 1744776 reaction equation
[C@@H:1]12[CH2:7][C:6](=[CH:8][C:9]([OH:11])=[O:10])[C@@H:5]1[CH2:4][CH2:3][CH2:2]2.S(=O)(=O)(O)O.[OH-].[Na+].[CH3:19][CH2:20]CCCCC>C(O)C.O>[C@@H:1]12[CH2:7][C:6](=[CH:8][C:9]([O:11][CH2:19][CH3:20])=[O:10])[C@@H:5]1[CH2:4][CH2:3][CH2:2]2

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 8900HeptaneHCID 14798Sodium HydroxideHCID 69590731HCID 69590731, compound

Product 1

HCID 91119464HCID 91119464, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

The compound of Example 5 (10.5 Kg; 69.0 mol) was dissolved in absolute ethanol (52.5 L) and 98 wt % sulfuric acid (0.525 Kg; 5.36 mol) was added at 20–25° C. The reaction mixture was then heated to 75° C. over 0.5 hours and stirred for 24 hours. The reaction mixture was cooled to 10° C. and a 40 wt % solution of sodium hydroxide (3.17 L) diluted with demineralised water (28.6 L) was added slowly to maintain the reaction temperature below 20° C. n-Heptane (31.5 L) was added and the phases were separated. The aqueous phase was then extracted again with n-heptane (31.5 L). The combined organic phases were washed twice with demineralised water (63.0 L, then 31.5 L). The organic phase was separated to give the title compound (11.1 Kg) in 89% yield as an organic solution which is used directly in the next step.

Workup

  1. temperatureThe reaction mixture was cooled to 10° C.
  2. additionwas added slowly
  3. additionwas added
  4. customthe phases were separated
  5. extractionThe aqueous phase was then extracted again with n-heptane (31.5 L)
  6. washThe combined organic phases were washed twice with demineralised water (63.0 L
  7. customThe organic phase was separated

Sources & evidence

ORD record
ord-ddc1d3a66fcf4564930eb3ca9fb2fbdb
Source dataset
uspto-grants-2006_03
Patent number
US07018818B2

Reaction notes

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