Sodium Hydroxide → HCID 9955206, compound

HRID 275979Notes

Reaction equation

HRID 275979 reaction equation
[OH-].[Na+].[CH:3]1[C:14]2[C:13](=[CH:15][CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([O:31][CH2:32][CH3:33])[C:26]([O:28]CC)=[O:27])=[CH:20][CH:19]=3)[C:12]3[CH:34]=[CH:35][CH:36]=[CH:37][C:11]=3[O:10][CH2:9][O:8][C:7]=2[CH:6]=[CH:5][CH:4]=1>C(O)C>[CH:3]1[C:14]2[C:13](=[CH:15][CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([O:31][CH2:32][CH3:33])[C:26]([OH:28])=[O:27])=[CH:20][CH:19]=3)[C:12]3[CH:34]=[CH:35][CH:36]=[CH:37][C:11]=3[O:10][CH2:9][O:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 9804934HCID 9804934, compound

Product 1

HCID 9955206HCID 9955206, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 15% aqueous solution of NaOH (4 ml) was added to a solution of ethyl 3-(4-(2-(12H-dibenzo(d,g)-1,3-dioxocine-12-ylidene)ethoxy)phenyl)-2-ethoxypropionate (0.95 g, 2.0 mmol) in ethanol (15 ml), and the mixture stirred at room temperature for 2 h, then left to stand overnight. The resulting solution was evaporated, water (20 ml) and benzene (25 ml) were added, and the mixture acidified to pH 6 with acetic acid. The benzene layer was separated, and the water layer further extracted with benzene (2×10 ml). The combined benzene extracts were washed with water (20 ml), brine (15 ml), dried (MgSO4) and evaporated to give 3-(4-(2-(12H-dibenzo(d,g)-1,3-dioxocine-12-ylidene)ethoxy)phenyl)-2-ethoxypropionic acid: 0.79 g (83.2%)

Workup

  1. waitleft
  2. waitto stand overnight
  3. customThe resulting solution was evaporated
  4. additionwater (20 ml) and benzene (25 ml) were added
  5. customThe benzene layer was separated
  6. extractionthe water layer further extracted with benzene (2×10 ml)
  7. washThe combined benzene extracts were washed with water (20 ml), brine (15 ml)
  8. dry with materialdried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-f44c5a5ff1a7481096f18c821a486ae5
Source dataset
uspto-grants-2002_03
Patent number
US06353018B1

Reaction notes

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