Sodium Hydroxide → HCID 15462418, compound

HRID 1275034Notes

Reaction equation

HRID 1275034 reaction equation
C([O:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]1[C:11]1[C:16]([O:17][CH3:18])=[CH:15][C:14]([O:19][CH3:20])=[C:13]([C:21](=[O:23])[CH3:22])[C:12]=1[OH:24])(=O)C.[OH-].[Na+].C(OCC)(=O)C.C(Cl)(Cl)Cl.COC1C=CC(C=O)=CC=1>CO>[C:21]([C:13]1[C:12]([OH:24])=[C:11]([C@@H:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C@H:5]2[OH:4])[C:16]([O:17][CH3:18])=[CH:15][C:14]=1[O:19][CH3:20])(=[O:23])[CH3:22]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 312444-MethoxybenzaldehydeHCID 21584013Chloroform ethylacetateHCID 22868492HCID 22868492, compound

Product 1

HCID 15462418HCID 15462418, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of trans-2-(3-acetyl-4,6,-dimethoxy-2-hydroxyphenyl)cyclohexyl acetate (IV; 43 g; 0.128 mol) in methanol (460 ml) was added a solution of sodium hydroxide (20%; 154 ml) using the addition funnel and allowed to stir at room temperature for 15 min. The reaction mixture was then heated to 60° C. and the progress of the reaction monitored by TLC (tlc system 10% ethyl acetate-chloroform; anisaldehyde spray; pdt. Rf value 0.3). Complete consumption of the starting material was seen after stirring at 60° C. for 3 hours. The reaction mixture was then cooled in an ice bath and neutralized with 2N HCl. The precipitated solid was filtered and dried at high vacuum (dry solid 32 g). The filtrate was concentrated in-vacuo to remove methanol and extracted with ethyl acetate. The ethyl acetate layer was washed with water, brine and dried over sodium sulphate. It was concentrated and chromatographed over silica gel (eluent 3% ethyl acetate-chloroform) to get 3 g of the title compound. In total, 35 g of the title compound was isolated (yield 93%; mp. 162-64° C.).

Workup

  1. temperatureThe reaction mixture was then heated to 60° C.
  2. customComplete consumption of the starting material
  3. stirringafter stirring at 60° C. for 3 hours
  4. temperatureThe reaction mixture was then cooled in an ice bath
  5. filtrationThe precipitated solid was filtered
  6. dry with materialdried at high vacuum (dry solid 32 g)
  7. concentrationThe filtrate was concentrated in-vacuo
  8. customto remove methanol
  9. extractionextracted with ethyl acetate
  10. washThe ethyl acetate layer was washed with water, brine
  11. dry with materialdried over sodium sulphate
  12. concentrationIt was concentrated
  13. customchromatographed over silica gel (eluent 3% ethyl acetate-chloroform)

Sources & evidence

ORD record
ord-4dcdbd6f44734669a93ec4bc0b2211df
Source dataset
uspto-grants-2000_12
Patent number
US06159988

Reaction notes

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