Sodium Hydroxide → 4-[2-(3,4-Bis-methoxymethoxy-phenyl)-vinyl]-benzoic Acid

HRID 1866454Notes

Reaction equation

HRID 1866454 reaction equation
C([O:3][C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][O:21][CH3:22])=[C:15]([O:23][CH2:24][O:25][CH3:26])[CH:14]=2)=[CH:7][CH:6]=1)C.[OH-].[Na+]>CO>[CH3:26][O:25][CH2:24][O:23][C:15]1[CH:14]=[C:13]([CH:12]=[CH:11][C:8]2[CH:7]=[CH:6][C:5]([C:4]([OH:27])=[O:3])=[CH:10][CH:9]=2)[CH:18]=[CH:17][C:16]=1[O:19][CH2:20][O:21][CH3:22]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 689779464-[2-(3,4-Bis-methoxymethoxy-phenyl)-vinyl]benzoic acid ethyl ester

Product 1

HCID 689762374-[2-(3,4-Bis-methoxymethoxy-phenyl)-vinyl]-benzoic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-[2-(3,4-bis-methoxymethoxy-phenyl)-vinyl]-benzoic acid ethyl ester (1.0 mmol) in MeOH (20 mL) was added 10% NaOH solution (3 eq). The resulting suspension was vigorously stirred for 8 h at room temperature. The mixture was then quenched by adding saturated NaH2PO4 (50 mL). The mixture was extracted with EtOAc (3×50 mL) and the combined organic layers were dried over Na2SO4. The crude product was purified on a short silica gel column.

Workup

  1. customThe mixture was then quenched
  2. additionby adding saturated NaH2PO4 (50 mL)
  3. extractionThe mixture was extracted with EtOAc (3×50 mL)
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. customThe crude product was purified on a short silica gel column

Sources & evidence

ORD record
ord-0397823b41414ec58b0699f5d70c729b
Source dataset
uspto-grants-2009_12
Patent number
US07629375B2

Reaction notes

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