Trifluoroacetate → 3'H-Spiro[cyclohexane-1,1'-isobenzofuran]-4-one

HRID 432596Notes

Reaction equation

HRID 432596 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1([OH:19])[CH2:18][CH2:17][C:12]2([O:16]CCO2)[CH2:11][CH2:10]1.FC(F)(F)C([O-])=O>CCCCCC.CCOCC>[C:9]12([CH2:10][CH2:11][C:12](=[O:16])[CH2:17][CH2:18]1)[C:4]1[C:3](=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:2][O:19]2

Participants

4

Reactant 2

HCID 84468TrifluoroacetateHCID 187600538-[2-(Hydroxymethyl)phenyl]-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 187601133'H-Spiro[cyclohexane-1,1'-isobenzofuran]-4-oneYield 44%

Reagents, catalysts & solvents 1

HCID 21584099Diethylether hexaneSolvent

Procedure

0.64 g (2.62 mmol) of 8-(2-Hydroxymethyl-phenyl)-1,4-dioxa-spiro[4.5]decan-8-ol was added to 80% trifluoroacetate (TFA) 2.5 ml. The mixture was stirred at room temperature for 5 hours. Rotory evaporation of the TFA left thick brown oil. The oil was dissolved in 2.0 ml of EtOAc and washed first with 1N NaOH and then with H2O. The organic layer was dried with MgSO4 and concentrated, leaving a thick yellow oil. Hexane/ether (2:1) was added and the sides of the flask were scratched. A precipitate began to form. 0.23 Grams of 3′H-Spiro[cyclohexane-1,1′-isobenzofuran]-4-one were obtained, 44% yield.

Workup

  1. customRotory evaporation of the TFA
  2. waitleft thick brown oil
  3. dissolutionThe oil was dissolved in 2.0 ml of EtOAc
  4. washwashed first with 1N NaOH
  5. dry with materialThe organic layer was dried with MgSO4
  6. concentrationconcentrated
  7. customleaving a thick yellow oil
  8. customto form

Sources & evidence

ORD record
ord-f1168dc3b88040e0bdff1ff2f0caefdd
Source dataset
uspto-grants-2003_12
Patent number
US06664258B1

Reaction notes

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