Sulfuric Acid → HCID 21413992, compound

HRID 1947188Notes

Reaction equation

HRID 1947188 reaction equation
[C:1](O)([CH3:4])([CH3:3])[CH3:2].[OH:6][C:7]1[CH:15]=[C:14]([OH:16])[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].FC(F)(F)C(O)=O.S(=O)(=O)(O)O>CCCCCC>[C:1]([C:13]1[C:14]([OH:16])=[CH:15][C:7]([OH:6])=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 14912,4-Dihydroxybenzoic AcidHCID 6386tert-ButanolHCID 6422Trifluoroacetic acid2×

Product 1

HCID 21413992HCID 21413992, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a tert-butanol (14.3 mL, 11.12 g, 150 mmol) suspension of 2,4-dihydroxy-benzoic acid (F71-01: 2312 mg, 15.0 mmol), trifluoroacetic acid (8.0 mL, 11.84 g, 103.8 mmol) and sulfuric acid (0.43 mL, 0.79 g, 8.0 mmol) were added in this order under argon atmosphere while stirring at room temperature. The reacting solution was stirred at room temperature for 10 minutes and then at a bath temperature of 75° C. for 6 hours. Additional trifluoroacetic acid (8.0 mL, 11.84 g, 103.8 mmol) was added, and the reaction mixture was stirred at a bath temperature of 80° C. for further 2.5 hours. After completing the reaction, the reaction mixture was added to ice-water (160 mL) and stirred with the addition of hexane (20 mL). The deposited solids were collected by filtration, washed with water and hexane to obtain the title compound (F71-02: pale pink solid, 2.13 g, 68%).

Workup

  1. additionwere added in this order under argon atmosphere
  2. stirringThe reacting solution was stirred at room temperature for 10 minutes
  3. stirringthe reaction mixture was stirred at a bath temperature of 80° C. for further 2.5 hours
  4. customthe reaction
  5. filtrationThe deposited solids were collected by filtration
  6. washwashed with water and hexane

Sources & evidence

ORD record
ord-ccbe64b4af6a4411b6660af3378f532f
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

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