Catechol → SBB059257

HRID 1288043Notes

Reaction equation

HRID 1288043 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[OH-:9].[Na+].Cl[CH2:12][CH2:13][O:14][CH2:15][CH2:16]Cl.Cl>O>[O:14]([CH2:15][CH2:16][O:9][C:8]1[CH:7]=[CH:6][CH:5]=[CH:3][C:1]=1[OH:2])[CH2:13][CH2:12][O:2][C:1]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4]

Participants

6

Reactant 4

HCID 289CatecholHCID 313Hydrochloric AcidHCID 8115Bis(2-chloroethyl) ether2×HCID 14798Sodium Hydroxide

Product 1

HCID 300689SBB059257Yield 23%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A vigorously agitated mixture of 220 grams (2 gram-mols) of catechol, 2000 ml. of water, 80 grams (2 gram-mols) of sodium hydroxide and 143 grams (1 grammol) of bis(beta-chloroethyl)ether is reacted at reflux at 102°-103°C. for 16 hours under nitrogen. It is then acidified with concentrated hydrochloric acid. When unreacted bis(2-chloroethyl)ether and 1000 ml. of water have been removed by distillation, the mixture separates into two layers. The organic layer is recovered and treated with 700 ml. of methanol and chilled with ice water. The crystals that subsequently form are filtered off, washed with cold methanol, and dried. The 2,2'-(oxydiethylenedioxy)-diphenol product, 67 to 74 grams (23 to 25.5% yield), melts at 85°C. and analyzes as follows (a typical example.

Workup

  1. temperatureat reflux at 102°-103°C. for 16 hours under nitrogen
  2. customof water have been removed by distillation
  3. customThe organic layer is recovered
  4. additiontreated with 700 ml
  5. temperatureof methanol and chilled with ice water
  6. filtrationThe crystals that subsequently form are filtered off
  7. washwashed with cold methanol
  8. customdried

Sources & evidence

ORD record
ord-ab58cb50e3414032a7f3668e0aec3269
Source dataset
uspto-grants-1976_10
Patent number
US03987061

Reaction notes

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