Acetone → Tert-butyl 4-vinylphenoxyacetate

HRID 743918

Reaction equation

HRID 743918 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[OH:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[CH2:22])=[CH:19][CH:18]=1.CC(C)=O>CCOCC.[I-].[K+]>[CH:21]([C:20]1[CH:23]=[CH:24][C:17]([O:16][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:18][CH:19]=1)=[CH2:22]

Participants

7

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 624534-VinylphenolHCID 79177tert-Butyl bromoacetate

Product 1

HCID 18762166Tert-butyl 4-vinylphenoxyacetateYield 98.5%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 3283Diethyl EtherSolvent

Procedure

59.3 g (430 mmol) of potassium carbonate, 0.64 g of potassium iodide, 50.7 g (260 mmol) of tert-butyl bromoacetate and 31.2 g (260 mmol) of 4-hydroxystyrene are mixed with 145 ml of acetone in a 750 ml sulfonation flask. The resultant suspension is refluxed for 100 minutes, cooled, filtered and evaporated. The residue obtained is taken up in 750 ml of ether and washed twice with 100 ml of 1N NaOH solution in each case and then twice with 200 ml of water in each case. The organic phase is separated off, dried over magnesium sulfate and evaporated, leaving 60.02 g (256 mmol) of the desired product as a clear oil, which corresponds to a yield of 98.5% of theory. 1H-NMR (CDCl3, 300 MHz): δ ppm] 7.33/d/2H of the resultant product 6,84/d/2H 6,64/dd/1H 5,60/d/1H 5,12/d/1H 4,49/s/2H 1,47/s/9H

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. customevaporated
  4. customThe residue obtained
  5. washwashed twice with 100 ml of 1N NaOH solution in each case
  6. customThe organic phase is separated off
  7. dry with materialdried over magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-4e0743878087423c9cb1b41bf7471d5d
Source dataset
uspto-grants-1996_09
Patent number
US05558978

Linked notes

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