Hydroquinone → 4-((6-(Acryloyloxy)hexyl)oxy)benzoic acid

HRID 1650599Notes

Reaction equation

HRID 1650599 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].O[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=1.C1(C=CC(O)=CC=1)O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.O.O.C([O-])(=O)C.[Na+]>O.C(Cl)(Cl)Cl>[C:1]([O:5][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([C:18]([OH:20])=[O:19])=[CH:21][CH:22]=1)(=[O:4])[CH:2]=[CH2:3]

Participants

8

Reactant 5

HCID 785HydroquinoneHCID 6101p-Toluenesulfonic acidHCID 6581Acrylic AcidHCID 36284134-(6-Hydroxyhexyloxy)benzoic acidHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 37135654-((6-(Acryloyloxy)hexyl)oxy)benzoic acidYield 79.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Conditions

Temperature
4 °C

Procedure

90.1 g of acrylic acid (1.25 mol), 29.8 g of 4-(6-hydroxyhexyloxy)benzoic acid, 4.5 g of hydroquinone, 4.5 g of p-toluenesulfonic acid and 300 ml of chloroform were placed in a sulfonation flask having a stirrer, water separator and reflux condenser. The mixture was heated to reflux for about 20 hours and then treated with a solution of 3.25 g of sodium acetate trihydrate in 10 ml of water. The chloroform and the excess acrylic acid were subsequently distilled off on a rotary evaporator. The residue was taken up in 1.5 1 of chloroform. The mixture was stirred for 2 hours and then filtered. The filtrate was washed three times with 200 ml of water each time, dried over sodium sulfate, filtered and concentrated. The residue was dissolved in 500 ml of toluene and the solution was again filtered. The filtrate was cooled to 4° C. for 12 hours and then to -20° C. for a further 12 hours. The crystalline product obtained was removed by filtration under suction, washed twice with cold toluene and again recrystallized from 400 ml of toluene. After drying at 60° C./40 mbar there were obtained 29.2 g of 4-(6-acrylyloxyhexyloxy)benzoic acid with m.p. (C-N) 92° C. and cl.p. (N-I) 110° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for about 20 hours
  3. distillationThe chloroform and the excess acrylic acid were subsequently distilled off on a rotary evaporator
  4. filtrationfiltered
  5. washThe filtrate was washed three times with 200 ml of water each time
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. dissolutionThe residue was dissolved in 500 ml of toluene
  10. filtrationthe solution was again filtered
  11. waitto -20° C. for a further 12 hours
  12. customThe crystalline product obtained
  13. customwas removed by filtration under suction
  14. washwashed twice with cold toluene
  15. customagain recrystallized from 400 ml of toluene
  16. customAfter drying at 60° C./40 mbar there

Sources & evidence

ORD record
ord-d408d2ab7fc84163a18cb40d3fba4bdc
Source dataset
uspto-grants-1990_05
Patent number
US04925589

Reaction notes

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