Potassium Hydroxide → HCID 22345521, compound

HRID 1700946Notes

Reaction equation

HRID 1700946 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:33]=[CH:32][C:25]([O:26][CH2:27][C:28]([O:30]C)=[O:29])=[CH:24][CH:23]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C>[Si:1]([O:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:33]=[CH:32][C:25]([O:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:24][CH:23]=1)([C:14]([CH3:15])([CH3:16])[CH3:17])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 22949948HCID 22949948, compound

Product 1

HCID 22345521HCID 22345521, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of methyl [4-[3-(tert-butyldiphenylsilyloxy)propyl]phenoxy]acetate (4.36 g, 9.4 mmol) in 80% aqueous ethanol (100 ml) was treated with potassium hydroxide (2 g) and the resulting mixture was heated at 50° C. for 2 h. The solvent was then evaporated in vacuo. Ice water and ethyl acetate were added and the aqueous phase was carefully adjusted to pH4 with 1N hydrochloric acid. The organic phase was then washed with brine, dried (magnesium sulfate) and evaporated under reduced pressure to give a white solid. Recrystallization from hexane gave 3.41 g (81%) of the title acid as white crystals: mp 87-88° C.

Workup

  1. customThe solvent was then evaporated in vacuo
  2. additionIce water and ethyl acetate were added
  3. washThe organic phase was then washed with brine
  4. dry with materialdried (magnesium sulfate)
  5. customevaporated under reduced pressure
  6. customto give a white solid
  7. customRecrystallization from hexane
  8. customgave 3.41 g (81%) of the title acid as white crystals

Sources & evidence

ORD record
ord-4b8b10339b204caba8f8194cdd16cd4e
Source dataset
uspto-grants-2002_02
Patent number
US06350892B1

Reaction notes

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