Ethylparaben → Ethyl p-(6-Bromohexyloxy)benzoate

HRID 2395537Notes

Reaction equation

HRID 2395537 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]Br.C([O-])([O-])=O.[K+].[K+]>>[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 8434EthylparabenHCID 11430Potassium CarbonateHCID 123681,6-Dibromohexane

Product 1

HCID 18989362Ethyl p-(6-Bromohexyloxy)benzoate

Procedure

An amount of 16.6 g (100 mmol) of ethyl 4-hydroxybenzoate, 122 g (500 mmol) of 1,6-dibromohexane, 10.0 g of K2CO3 (finely powdered in a mortar and dried) are heated under reflux in 75 ml of absolute acetone. After 20 hours, first the acetone and then the excess of dibromohexane are removed by distillation at 15 mmHg. The crude product is purified in a high vacuum by means of a bulb tube distillation apparatus. After recrystallization from a little ethanol and drying in vacuo over P4O10, about 10 g of analytically pure product are obtained. The melting point is in the room temperature range.

Workup

  1. customdried)
  2. temperatureare heated
  3. temperatureunder reflux in 75 ml of absolute acetone
  4. customfirst the acetone and then the excess of dibromohexane are removed by distillation at 15 mmHg
  5. customThe crude product is purified in a high vacuum by means of a bulb tube
  6. distillationdistillation apparatus
  7. customAfter recrystallization from a little ethanol
  8. dry with materialdrying in vacuo over P4O10, about 10 g of analytically pure product
  9. customare obtained
  10. customis in the room temperature range

Sources & evidence

ORD record
ord-295dce2caaac487683388e720e78a64f
Source dataset
uspto-grants-1996_02
Patent number
US05489585

Reaction notes

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