Oxalic Acid → Alpha,alpha'-bis(2,4-dihydroxyphenyl)-1,3-diisopropylbenzene

HRID 1463435Notes

Reaction equation

HRID 1463435 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[C:9]([OH:14])(=O)[C:10](O)=O.[C:15]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([CH3:26])=[CH2:25])[CH:19]=1)([CH3:17])=[CH2:16]>CCCCCCC>[OH:2][C:1]1[CH:3]=[C:4]([OH:5])[CH:6]=[CH:7][C:8]=1[C:24]([C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([C:15]([C:3]2[CH:4]=[CH:10][C:9]([OH:14])=[CH:8][C:1]=2[OH:2])([CH3:17])[CH3:16])[CH:19]=1)([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 5054ResorcinolHCID 773531,3-Diisopropenylbenzene

Product 1

HCID 10861765Alpha,alpha'-bis(2,4-dihydroxyphenyl)-1,3-diisopropylbenzene

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Conditions

Temperature
75 °C

Procedure

Into a 2-liter kettle equipped with stirrer, thermometer, reflux condenser and an addition funnel, 264.0 grams of resorcinol (2.4 moles) 12.0 grams of oxalic acid and 900 ml of heptane were placed. The contents of this flask were heated to about 75° C. While maintaining the temperature of the resorcinolic slurry between about 75°-85° C., 126.4 grams of 1,3-diisopropenyl benzene (0.8 moles) was added dropwise for about 2 hours. After the completion of the above addition, the temperature of the reaction mixture was raised to and maintained at about 95° C. for about an additional 2.0 hours, while the reaction mixture was continuously stirred. The reaction mixture was then cooled and the separated heptane layer was removed by decantation. Finally the solidified mass was treated with excess dichloromethane to separate the reaction product. The white precipitate that separated from the solution was filtered, washed with dichloromethane and then washed with distilled water. After air drying at about room temperature the precipitate weighed 215 grams. Structural characterization by IR/NMR analysis of the reaction product confirmed the structure of 1,3-bis[(2,4-di-hydroxyphenyl)-alpha-methyl ethyl] benzene.

Workup

  1. customInto a 2-liter kettle equipped with stirrer
  2. temperaturethermometer, reflux condenser and an addition funnel
  3. temperatureWhile maintaining the temperature of the resorcinolic slurry between about 75°-85° C.
  4. additionAfter the completion of the above addition
  5. temperaturethe temperature of the reaction mixture was raised to and
  6. temperaturemaintained at about 95° C. for about an additional 2.0 hours, while the reaction mixture
  7. temperatureThe reaction mixture was then cooled
  8. customthe separated heptane layer was removed by decantation
  9. additionFinally the solidified mass was treated with excess dichloromethane
  10. customto separate the reaction product
  11. customThe white precipitate that separated from the solution
  12. filtrationwas filtered
  13. washwashed with dichloromethane
  14. washwashed with distilled water
  15. customAfter air drying at about room temperature the precipitate

Sources & evidence

ORD record
ord-39c4f8351a254d4c85f4414220c3368c
Source dataset
uspto-grants-1994_04
Patent number
US05300618

Reaction notes

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