4-Hydroxybenzaldehyde → 1,2-Ethanediol, 1,2-bis(4-hydroxyphenyl)-

HRID 371604Notes

Reaction equation

HRID 371604 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1>[OH-].[Na+]>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([OH:7])[CH:6]([C:5]2[CH:8]=[CH:9][C:2]([OH:1])=[CH:3][CH:4]=2)[OH:7])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 1264-Hydroxybenzaldehyde

Product 1

HCID 1073801,2-Ethanediol, 1,2-bis(4-hydroxyphenyl)-Yield 74.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
45 °C

Procedure

The electrolysis cell was charged with 400 grams (3.28 moles) of 4-hydroxybenzaldehyde and 3500 milliliters 2.0 molar aqueous sodium hydroxide. The mixture was warmed on a stirrer-hotplate to about 45° C to effect complete dissolution. Then a small amount of Union Carbide SAG 470 silicone antifoam agent was added. The electrolysis was conducted at a constant current of 25 amperes and a temperature range between about 44° C and about 49° C over an 8-hour period. The cathode potential was -2.0 to about -2.1 volts versus the saturated calomel electrode. Upon completion of the electrolysis, the product solution was allowed to cool to ambient temperatures and removed from the cell. The cell was washed with water and the washings added to the product solution. The volume of the combined product solution and washings was reduced to approximately 1,500 milliliters by evaporation in vacuo. The remaining solution was acidified to about pH 6.3 by the dropwise addition of acetic acid at the rate of 20 milliliters per minute. A total of 450 milliliters of acetic acid was added. The solution was cooled in an ice-water bath to induce crystallization. The precipitate was collected by suction filtration, washed with cold water, and dried to yield 299.0 grams (74.1 percent) of 1,2-bis(4-hydroxyphenyl)-ethane-1,2-diol.

Workup

  1. dissolutiondissolution
  2. waita temperature range between about 44° C and about 49° C over an 8-hour period
  3. temperatureto cool to ambient temperatures
  4. customremoved from the cell
  5. washThe cell was washed with water
  6. additionthe washings added to the product solution
  7. customThe volume of the combined product solution and washings was reduced to approximately 1,500 milliliters by evaporation in vacuo
  8. additionThe remaining solution was acidified to about pH 6.3 by the dropwise addition of acetic acid at the rate of 20 milliliters per minute
  9. additionA total of 450 milliliters of acetic acid was added
  10. temperatureThe solution was cooled in an ice-water bath
  11. customcrystallization
  12. filtrationThe precipitate was collected by suction filtration
  13. washwashed with cold water
  14. customdried

Sources & evidence

ORD record
ord-3dce4c86b9d04badb8463383890d4140
Source dataset
uspto-grants-1978_05
Patent number
US04087336

Reaction notes

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