Protocatechuic Acid → HCID 131730573, compound

HRID 2093256Notes

Reaction equation

HRID 2093256 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1O)[C:5]([OH:7])=[O:6].CC(C)[O-:14].[Ti+4:16].CC(C)[O-:19].CC(C)[O-].CC(C)[O-]>C1(C)C=CC=CC=1>[C:5]([C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([O-:1])[C:3]=1[O-:14])([OH:7])=[O:6].[Ti+4:16].[C:5]([C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([O-:1])[C:3]=1[O-:19])([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 72Protocatechuic AcidHCID 11026Titanium isopropoxide

Product 1

HCID 131730573HCID 131730573, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 3,4-dihydroxybenzoic acid (30.8 g, 200 mmol) and toluene (220 ml) was dehydrated by distilling 20 mL of the solution. Thereafter, 28.4 g (100 mmol) of titanium(IV) isopropoxide (TTIP) was added to the solution while stirring. The mixed solution was refluxed for 1 hour, and then, while the distillation temperature was 100° C. or higher, distilled until the amount of the solution became half. After the distillation, solid content of the product was isolated by suction filtering using a membrane suction filter. The residual solid content was heated to 100° C. under vacuum using a vacuum dryer so that remaining volatile components were completely removed. The solid content (3,4-dihydroxybenzoic acid-titanium complex) was brown in color. The yield amount was 35.0 g (99.4 mmol), and the yield percentage was 99%. 3.52 g of 3,4-dihydroxybenzoic acid-titanium complex was dissolved into 100 mL of 1:4 acetylacetone/ethyl acetate to produce a coating liquid.

Workup

  1. distillationby distilling 20 mL of the solution
  2. temperatureThe mixed solution was refluxed for 1 hour
  3. customwas 100° C.
  4. distillationhigher, distilled until the amount of the solution
  5. distillationAfter the distillation, solid content of the product
  6. customwas isolated by suction
  7. filtrationfiltering
  8. filtrationfilter
  9. customwere completely removed
  10. dissolution3.52 g of 3,4-dihydroxybenzoic acid-titanium complex was dissolved into 100 mL of 1:4 acetylacetone/ethyl acetate
  11. customto produce a coating liquid

Sources & evidence

ORD record
ord-81b15c983ce94d1088872bec8fe18798
Source dataset
uspto-grants-2013_05
Patent number
US08445118B2

Reaction notes

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