Sodium Hydroxide → HCID 11811825, compound

HRID 1841289Notes

Reaction equation

HRID 1841289 reaction equation
[CH2:1]([O:3][CH:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH:20]2[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[O:27][C:26]3[C:21]2=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:13][CH:12]=1)[C:5]([O:7]CC)=[O:6])[CH3:2].[OH-].[Na+]>C(O)C>[CH2:1]([O:3][CH:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH:20]2[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[O:27][C:26]3[C:21]2=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:13][CH:12]=1)[C:5]([OH:7])=[O:6])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11730000HCID 11730000, compound

Product 1

HCID 11811825HCID 11811825, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-ethoxy-3-{4-[2-(9H-xanthen-9-yl)ethoxy]phenyl}propionate (1.8 g, 4.03 mmol) in ethanol (15 ml) was added a 15% solution of NaOH (4 ml), and the mixture was stirred at room temperature for 5 h, then left to stand overnight. The resulting solution was evaporated, water (50 ml) was added, the mixture was acidified with 15% hydrochloric acid to pH 2, and the products extracted into Et2O (4×30 ml). The combined extracts were washed with water (30 ml), brine (15 ml), dried (MgSO4) and evaporated to give the title compound as an oil: 1.3 g (77.1%).

Workup

  1. waitleft
  2. waitto stand overnight
  3. customThe resulting solution was evaporated
  4. additionwater (50 ml) was added
  5. extractionthe products extracted into Et2O (4×30 ml)
  6. washThe combined extracts were washed with water (30 ml), brine (15 ml)
  7. dry with materialdried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-2ad43cae23584f1d87d208462f3ed7d0
Source dataset
uspto-grants-2004_01
Patent number
US06683111B2

Reaction notes

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