Methanol → HCID 66761798, compound

HRID 561860Notes

Reaction equation

HRID 561860 reaction equation
[Cl:1][C:2]1[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([Cl:27])[C:3]=1[O:4][CH2:5][CH2:6][O:7][C:8]1[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=1CC(=C)CCC([O-])=O.[CH3:28][OH:29].[OH-:30].[Li+]>C1COCC1>[Cl:27][C:22]1[CH:23]=[C:24]([CH3:26])[CH:25]=[C:2]([Cl:1])[C:3]=1[O:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:18][C:19]([CH2:24][CH:25]([CH2:2][CH:3]=[CH2:22])[C:28]([OH:30])=[O:29])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 86635927HCID 86635927, compound

Product 1

HCID 66761798HCID 66761798, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-(4-{2-[(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}pent-4-enoate from the previous step (1 eq.) was dissolved in a 2:1 (v/v) THF:MeOH solution (0.06 M). To this was then added lithium hydroxide (1.0 M aqueous solution, 3.4 eq.) and the resulting solution was stirred at 50° C. for 12 h. The volatiles were then removed in vacuo. Following careful acidification of the resulting residue with 10% aq. HCl, the mixture was extracted with EtOAc. The combined organic extracts were washed with H2O and brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded the title compound as a viscous oil.

Workup

  1. customThe volatiles were then removed in vacuo
  2. extractionthe mixture was extracted with EtOAc
  3. washThe combined organic extracts were washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered

Sources & evidence

ORD record
ord-b7f3714db56041bf85925c6d813e507b
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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