Sulfuric Acid → HCID 22493863, compound

HRID 1816424Notes

Reaction equation

HRID 1816424 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([OH:14])[CH:5]=[CH:4][C:3]1=2.[F:16][C:17]([F:27])([F:26])[C:18](=O)[CH2:19][C:20](OCC)=[O:21].OS(O)(=O)=O>>[CH3:1][C:2]1([CH3:15])[C:3]2[CH:4]=[C:5]3[C:6](=[CH:7][C:8]=2[C:9]([CH3:13])([CH3:12])[CH2:10][CH2:11]1)[O:14][C:20](=[O:21])[CH:19]=[C:18]3[C:17]([F:27])([F:26])[F:16]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 2687865,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ol2×

Product 1

HCID 22493863HCID 22493863, compoundYield 38.2%

Conditions

Temperature
100 °C

Procedure

A mixture of 5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-ol (Intermediate 2, 4.12 g, 20.2 mmol), ethyl trifluoroacetoacetate (7.4 mL, 50.4 mmol), and H2SO4 (8 mL, 75%) was heated at 100° C. for 4 h. The mixture was poured onto ice, quenched with NaHCO3 and extracted with Et2O. The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was dissolved in Et2O, a readily crystalline side product precipitated and was removed by filtration. The filtrate was concentrated to give a residue. Recrystallization of the residue gave the title compound as white crystals (2.5 g, 38%).

Workup

  1. additionThe mixture was poured onto ice
  2. customquenched with NaHCO3
  3. extractionextracted with Et2O
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in Et2O
  8. customa readily crystalline side product precipitated
  9. customwas removed by filtration
  10. concentrationThe filtrate was concentrated
  11. customto give a residue
  12. customRecrystallization of the residue

Sources & evidence

ORD record
ord-d958a55e74b548c38c940b8b80b847d7
Source dataset
uspto-grants-2005_04
Patent number
US06884820B2

Reaction notes

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