Hydrochloric Acid → HCID 11184364, compound

HRID 1729891Notes

Reaction equation

HRID 1729891 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[C:14](=[O:18])[C:15]([OH:17])=[O:16].[Mg].[CH3:20]I.Cl>CCOCC.C(O)(=O)C>[CH3:20][C:14]([OH:18])([C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:12][C:13]=2[CH:1]=1)[C:15]([OH:17])=[O:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 5462224MagnesiumHCID 21406504Fluorene-2-glyoxylic acid

Product 1

HCID 11184364HCID 11184364, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A cooled solution of fluorene-2-glyoxylic acid (4.5 g) in ether (150 ml) is treated dropwise over a 45 minute period with Grignard reagent prepared from magnesium (2.1 g) and methyl iodide (6.5 ml) in ether (145 ml). The mixture is then stirred for 2 hours at room temperature and poured into ice water. The mixture is treated with 250 ml 50% acetic acid and finally acidified to pH 2.0 with 10% HCl. The ether layer is separated, and the aqueous extracted with additional ether. The combined ether extracts are washed with sodium chloride solution and water, dried (MgSO4) and evaporated to give the title compound (3.7 g, mp 164°-168°). Recrystallization from ethyl acetate-hexane raises the mp to 170°-171°, λKBr 3400 cm-1.

Workup

  1. customThe ether layer is separated
  2. extractionthe aqueous extracted with additional ether
  3. washThe combined ether extracts are washed with sodium chloride solution and water
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-5d4aa5b05e534573ac352d313daa649c
Source dataset
uspto-grants-1976_11
Patent number
US03989841

Reaction notes

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