Water → Tert-butyl 3-(2-isopropylphenoxy)propionate

HRID 1819503Notes

Reaction equation

HRID 1819503 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([CH3:3])[CH3:2].C(OC(C)(C)C)(C)(C)C.[K].O.[C:22]([O:26][C:27](=[O:30])[CH:28]=[CH2:29])([CH3:25])([CH3:24])[CH3:23]>>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:29][CH2:28][C:27]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:30])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 962WaterHCID 69432-IsopropylphenolHCID 15458tert-Butyl acrylateHCID 86607002Potassium tert-butyloxide

Product 1

HCID 23119473Tert-butyl 3-(2-isopropylphenoxy)propionateYield 36.9%

Conditions

Temperature
130 °C

Procedure

2-Isopropylphenol (6 g) was dissolved in acrylic acid tert-butyl ester (6.2 g), and to the mixture was added potassium tert-butyloxide (0.3 g). The reaction mixture was stirred at 130° C. for 6 h. To the reaction mixture was added water, the reaction mixture extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate=9:1) to obtain the compound (10) 4.3 g.

Workup

  1. extractionthe reaction mixture extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-f08906a112a2445eb2d6592526fe52b8
Source dataset
uspto-grants-2009_10
Patent number
US07601746B2

Reaction notes

Loading…