Sodium Hydroxide → 4-(3-(2,6-Dimethylbenzyloxy)phenyl)-4-oxo-2-butenoic acid

HRID 2276682Notes

Reaction equation

HRID 2276682 reaction equation
[CH3:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12](=[O:20])[CH:13]=[CH:14][C:15]([O:17]CC)=[O:16])[CH:9]=[CH:10][CH:11]=1.[OH-].[Na+]>C(O)C>[CH3:25][C:21]1[CH:22]=[CH:23][CH:24]=[C:2]([CH3:1])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12](=[O:20])[CH:13]=[CH:14][C:15]([OH:17])=[O:16])[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 73856874Ethyl 4-(3-(2,6-dimethylbenzyloxy)phenyl)-4-oxo-2-butenoate

Product 1

HCID 738568734-(3-(2,6-Dimethylbenzyloxy)phenyl)-4-oxo-2-butenoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of Ethyl 4-(3-(2,6-dimethylbenzyloxy)phenyl)-4-oxo-2-butenoate (Step E) in abs ethanol at low temp, add aqueous sodium hydroxide, after an hour, concentrate and purify by flash chromatography on silica gel column (chloroform:methanol 95:5 spiked with acetic acid).

Workup

  1. waitafter an hour
  2. concentrationconcentrate
  3. custompurify by flash chromatography on silica gel column (chloroform:methanol 95:5 spiked with acetic acid)

Sources & evidence

ORD record
ord-0125ec0609194a8c98226dade7967537
Source dataset
uspto-grants-2015_09
Patent number
US09133073B2

Reaction notes

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