Methanol → HCID 86740490, compound

HRID 1583254Notes

Reaction equation

HRID 1583254 reaction equation
C[O:2][C:3](=[O:23])[C:4]([CH3:22])([CH3:21])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].CO.O.[OH-].[Li+]>O>[CH3:21][C:4]([CH3:22])([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:3]([OH:23])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 86740491HCID 86740491, compound

Product 1

HCID 86740490HCID 86740490, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The material from Example 67 was treated with methyl alcohol (300 ml), lithium hydroxide monohydrate (6.3 g) and water (100 ml) and stirred for about 18 hrs. at room temperature. After warming on a hot plate for 6 hrs. and allowing to stir ovrnight at room temperature, the methyl alcohol was removed on a rotary evaporator and the aqueous residue acidified with 1N hydrochloric acid to pH 2. The product was extracted into ethyl acetate (2×100 ml), dried over sodium sulfate, filtered and stripped of solvent to yield an oil. The title compound was purified by chromatography on silica gel.

Workup

  1. customat room temperature
  2. temperatureAfter warming on a hot plate for 6 hrs
  3. stirringto stir ovrnight at room temperature
  4. customthe methyl alcohol was removed on a rotary evaporator
  5. extractionThe product was extracted into ethyl acetate (2×100 ml)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customto yield an oil
  9. customThe title compound was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-325390a73f274eca88cfd8635532a194
Source dataset
uspto-grants-1985_11
Patent number
US04551279

Reaction notes

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