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

HRID 2262808Notes

Reaction equation

HRID 2262808 reaction equation
[CH3:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH2:14][C:15]([O:17]CC)=[O:16])[CH:9]=[CH:10][CH:11]=1.[OH-].[Na+]>C(O)C>[CH3:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:2]([CH3:1])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH2:14][C:15]([OH:17])=[O:16])[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67274119Ethyl 4-(3-(2,6-dimethylbenzyloxy)phenyl)-3-butenoate

Product 1

HCID 672736064-(3-(2,6-Dimethylbenzyloxy)phenyl)-3-butenoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of Ethyl 4-(3-(2,6-dimethylbenzyloxy)phenyl)-3-butenoate (Step F) 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-4348aa28be5f4950b2f016720e543e7d
Source dataset
uspto-grants-2010_12
Patent number
US07851494B2

Reaction notes

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