o-Phenylenediacetic acid → 1,2-Benzenediethanol

HRID 621760Notes

Reaction equation

HRID 621760 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([CH2:17][C:18](O)=[O:19])[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][C:14](O)=[O:15]>O1CCCC1>[OH:15][CH2:14][CH2:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH2:17][CH2:18][OH:19]

Participants

4

Reactant 2

HCID 24123o-Phenylenediacetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 2519601,2-Benzenediethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (0.332 mol) and tetrahydrofuran (THF, 175 mL) are placed in a dry 500-mL three-necked round-bottom flask fitted with a condenser, addition funnel, nitrogen inlet, and magnetic stirrer. The mixture is cooled with an ice bath and 1.2-phenylene diacetic acid (0.165 mol) in THF (100 mL) is added dropwise to the stirring mixture. After the addition is complete, the flask is removed from the ice bath and allowed to warm to room temperature. The reaction mixture is heated at reflux for two hours, then stirred overnight at room temperature. After cooling the mixture with an ice bath, water (12.6 mL) is added dropwise, followed by the successive dropwise addition of 15 percent aqueous sodium hydroxide (12.6 mL) and water (38 mL). The resulting mixture is warmed to room temperature, and the solids separated by vacuum filtration. The filtrate is placed on a rotary evaporator to remove the solvent. The remaining solid is recrystallized from toluene-hexane to give the 1,2-di(hydroxyethyl)benzene.

Workup

  1. customfitted with a condenser, addition funnel, nitrogen inlet, and magnetic stirrer
  2. temperatureThe mixture is cooled with an ice bath
  3. additionAfter the addition
  4. customthe flask is removed from the ice bath
  5. temperatureThe reaction mixture is heated
  6. temperatureat reflux for two hours
  7. temperatureAfter cooling the mixture with an ice bath
  8. additionwater (12.6 mL) is added dropwise
  9. additionfollowed by the successive dropwise addition of 15 percent aqueous sodium hydroxide (12.6 mL) and water (38 mL)
  10. temperatureThe resulting mixture is warmed to room temperature
  11. customthe solids separated by vacuum filtration
  12. customThe filtrate is placed on a rotary evaporator
  13. customto remove the solvent
  14. customThe remaining solid is recrystallized from toluene-hexane

Sources & evidence

ORD record
ord-c8f923ffba0f43d8bc3d93b8c6b4332e
Source dataset
uspto-grants-1989_04
Patent number
US04824977

Reaction notes

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