Sodium Hydroxide → 2-(9H-fluoren-9-yloxy)acetic acid

HRID 1729246Notes

Reaction equation

HRID 1729246 reaction equation
[OH-].[Na+].[CH:3]1[C:15]2[CH:14]([O:16][CH2:17][C:18]([O:20]CC)=[O:19])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH:6]=[CH:5][CH:4]=1>C(O)C>[CH:12]1[C:13]2[CH:14]([O:16][CH2:17][C:18]([OH:20])=[O:19])[C:15]3[C:7](=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:8]=2[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19011665Ethyl 9-fluorenyloxyacetate

Product 1

HCID 190116622-(9H-fluoren-9-yloxy)acetic acidYield 86.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10 ml of 1N sodium hydroxide was added dropwise to a solution of 2.28 g of ethyl 9-fluorenyloxyacetate in 40 ml of ethanol, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated and water was added. After washing with ether, the pH value of the aqueous layer was adjusted with 18% hydrochloric acid to 3 to 4 under ice-cooling, followed by extraction with ether. The organic layer was dried over anhydrous magnesium sulfate, and concentrated to give 1.77 g of 9-fluorenyloxyacetic acid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added
  3. washAfter washing with ether
  4. temperaturecooling
  5. extractionfollowed by extraction with ether
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d314def3ad9140b6b83d53df58b3dd8a
Source dataset
uspto-grants-1994_07
Patent number
US05332734

Reaction notes

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