Hydrochloric Acid → Ethyl 2-(4-hydroxyphenoxy)-2-methylpropanoate

HRID 2234860Notes

Reaction equation

HRID 2234860 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].Br[C:10]([CH3:17])([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12].Cl>CN(C=O)C>[OH:2][C:1]1[CH:8]=[CH:7][C:5]([O:6][C:10]([CH3:17])([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 785HydroquinoneHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl ester

Product 1

HCID 181741Ethyl 2-(4-hydroxyphenoxy)-2-methylpropanoateYield 40.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

11 g of hydroquinone (100 mmol) in 100 ml of DMF is placed at 80° C. for 2 h. This mixture is cooled at ambient temperature then a solution of ethyl bromoisobutyrate (14.7 ml, 100 mmol) in 30 ml of DMF is added dropwise. The mixture is stirred for 3 h then the reaction medium is dry concentrated. The residue obtained is taken up in a 1 N HCl solution then extracted with AcOEt. The organic phases are washed with water, dried on MgSO4, then dry concentrated. The residue obtained is purified by flash chromatography on silica (petroleum ether:AcOEt 80:20). 9 g of oil corresponding to intermediate 10c are thus isolated (40% yield). TLC silica gel 60 F 254 Merck, petroleum ether:AcOEt 70:30, Rf=0.50.

Workup

  1. customthe reaction medium is dry
  2. concentrationconcentrated
  3. customThe residue obtained
  4. extractionthen extracted with AcOEt
  5. washThe organic phases are washed with water
  6. customdried on MgSO4
  7. customdry
  8. concentrationconcentrated
  9. customThe residue obtained
  10. customis purified by flash chromatography on silica (petroleum ether:AcOEt 80:20)

Sources & evidence

ORD record
ord-9eb6543dd17a495db853b8db58ec9196
Source dataset
uspto-grants-2010_05
Patent number
US07713971B2

Reaction notes

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