Sodium Hydroxide → CD2314

HRID 1126Notes

Reaction equation

HRID 1126 reaction equation
[CH3:1][C:2]1([CH3:28])[CH2:15][CH2:14][C:13]([CH3:17])([CH3:16])[C:12]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][C:8]([C:18]4[S:19][CH:20]=[C:21]([C:23]([O:25]CC)=[O:24])[CH:22]=4)=[CH:9]3)=[CH:4][C:3]1=2.[OH-].[Na+]>>[CH3:1][C:2]1([CH3:28])[CH2:15][CH2:14][C:13]([CH3:16])([CH3:17])[C:12]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][C:8]([C:18]4[S:19][CH:20]=[C:21]([C:23]([OH:25])=[O:24])[CH:22]=4)=[CH:9]3)=[CH:4][C:3]1=2

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 9821896Ethyl 2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)-4-thiophenecarboxylate

Product 1

HCID 15293210CD2314

Procedure

6.3 g (16 mmol) of the ester prepared in Example 1 and 100 ml of a 2N methanolic sodium hydroxide solution were introduced into a round-bottomed flask and the mixture was heated at reflux for one hour. The reaction medium was evaporated to dryness, the residue taken up in water, acidified to pH 1 with concentrated hydrochloric acid and the solids filtered. The product obtained was recrystallized from an ethyl alcohol/water mixture and 4.5 g (77%) of the expected acid of melting point 223°-225° C. were recovered.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for one hour
  3. customThe reaction medium was evaporated to dryness
  4. filtrationthe solids filtered
  5. customThe product obtained
  6. customwas recrystallized from an ethyl alcohol/water mixture and 4.5 g (77%) of the expected acid of melting point 223°-225° C.
  7. customwere recovered

Sources & evidence

ORD record
ord-66e0b8dbf3514265bd84740660b01c23
Source dataset
uspto-grants-1998_03
Patent number
US05723499

Reaction notes

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