Sodium Hydroxide → HCID 19013101, compound

HRID 1919751Notes

Reaction equation

HRID 1919751 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][C:10]=1[CH2:19][CH2:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=1[CH2:19][CH2:20][CH3:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53943964HCID 53943964, compound

Product 1

HCID 19013101HCID 19013101, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 4-benzyloxy-3-propylbenzoate (6.84 g, 24.1 mmol) and a sodium hydroxide solution (2 mol/L, 30 ml) in ethanol (100 mL) was heated under reflux for two hours. The reaction solution was concentrated and then made acidic with dilute hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was recrystallized (hexane-ethyl acetate) to obtain 6.35 g of the title compound (yield: 98%) as a white powder.

Workup

  1. temperatureunder reflux for two hours
  2. concentrationThe reaction solution was concentrated
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was recrystallized (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-f505cb3e5bac477f898c0a109027a1ad
Source dataset
uspto-grants-2012_05
Patent number
US08168666B2

Reaction notes

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