Hydrochloric Acid → Fluorene-2-glyoxylic acid

HRID 1729889Notes

Reaction equation

HRID 1729889 reaction equation
C([C:3]1[C:15]2[CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH:6]=[CH:5][C:4]=1[C:16](=[O:20])[C:17]([OH:19])=[O:18])C.[OH-].[Na+].Cl>C(O)C>[CH:3]1[C:15]2[CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH:6]=[CH:5][C:4]=1[C:16](=[O:20])[C:17]([OH:19])=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70633383HCID 70633383, compound

Product 1

HCID 21406504Fluorene-2-glyoxylic acidYield 79.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl fluorene-2-glyoxylic acid (9.95 g) and sodium hydroxide (1.60 g) in 50% aqueous ethanol (100 ml) is refluxed for 0.5 hour, cooled and acidified to pH 2.0 with 10% HCl. The reaction mixture is extracted with ether, and the ether extracts dried (MgSO4) and evaporated. The residue is crystallized from benzene-hexane (Darco) to give the title compound (7.1 g. mp 135°-137°). The analytical sample is prepared by recrystallization from benzenehexane: mp 139°-140°.

Workup

  1. temperatureis refluxed for 0.5 hour
  2. temperaturecooled
  3. extractionThe reaction mixture is extracted with ether
  4. dry with materialthe ether extracts dried (MgSO4)
  5. customevaporated
  6. customThe residue is crystallized from benzene-hexane (Darco)

Sources & evidence

ORD record
ord-e56d346dec194527bc86a0225a40aca9
Source dataset
uspto-grants-1976_11
Patent number
US03989841

Reaction notes

Loading…