Acetic Acid → HCID 57913857, compound

HRID 884331Notes

Reaction equation

HRID 884331 reaction equation
[CH3:1][C:2]1([CH3:30])[C:14]2[CH:13]=[C:12]([C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=[CH:17][C:16]=3C(OCC)=O)[CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[CH3:31][Li].[C:33]([OH:36])(=O)[CH3:34]>C1COCC1.C(OCC)C>[CH3:1][C:2]1([CH3:30])[C:14]2[CH:13]=[C:12]([C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=[CH:17][C:16]=3[C:33]([OH:36])([CH3:34])[CH3:31])[CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 57913689HCID 57913689, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 57913857HCID 57913857, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

100.6 g of ethyl 1-(9,9-dimethyl-9H-fluoren-2-yl)naphthalene-2-carboxylate (256 mmol) are initially introduced in 1000 ml of dried THF, 510 ml of a 1.5 M methyllithium solution in diethyl ether are added dropwise at −70° C., and the mixture is stirred at this temperature for 2 h. For work-up, 100 ml of ice-water followed by 300 ml of 50% acetic acid are added. The organic phase is separated off, washed twice with water, dried and evaporated in vacuo. The colourless solid which remains is recrystallised twice from heptane/toluene. Yield: 82 g (85%) of colourless crystals.

Workup

  1. additionare added
  2. customThe organic phase is separated off
  3. washwashed twice with water
  4. customdried
  5. customevaporated in vacuo
  6. customThe colourless solid which remains is recrystallised twice from heptane/toluene

Sources & evidence

ORD record
ord-5ca114b44b3046fd8fa154e819369435
Source dataset
uspto-grants-2012_08
Patent number
US08241763B2

Reaction notes

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