Sodium Hydroxide → HCID 44135424, compound

HRID 1408923Notes

Reaction equation

HRID 1408923 reaction equation
[OH-].[Na+].[CH3:3][C@@:4]1([C:15]([O:17]C)=[O:16])[CH2:8][CH2:7][C@@H:6]([C:9]([O:11]C)=[O:10])[C:5]1([CH3:14])[CH3:13]>CO>[CH3:3][C@@:4]1([C:15]([OH:17])=[O:16])[CH2:8][CH2:7][CH:6]([C:9]([OH:11])=[O:10])[C:5]1([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 6932371HCID 6932371, compound

Product 1

HCID 44135424HCID 44135424, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1 N aqueous solution of sodium hydroxide (36.8 mL, 36.8 mmol) was added to a solution of the crude di-ester mixture from Step 2 (1.4 g) in methanol (40 mL) at room temperature. The resulting mixture was heated to reflux for a total of 30 h then cooled to room temperature. After removal of methanol in vacuo, the aqueous residue was washed with dichloromethane (2×20 mL), acidified with 6 N hydrochloric acid and extracted with dichloromethane (3×80 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated to give the crude product (730 mg), which was taken to the next step without purification.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for a total of 30 h
  3. customAfter removal of methanol in vacuo
  4. washthe aqueous residue was washed with dichloromethane (2×20 mL)
  5. extractionextracted with dichloromethane (3×80 mL)
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a1040e65770847728d873daa1c86cee2
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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