Benzyl 4-Hydroxybenzoate → HCID 59556611, compound

HRID 1172925Notes

Reaction equation

HRID 1172925 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27]>CC(C)=O>[C:29]([O:28][C:26](=[O:27])[CH2:25][O:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1)([CH3:32])([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 7180Benzyl 4-HydroxybenzoateHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetate

Product 1

HCID 59556611HCID 59556611, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
65 °C

Procedure

In a 100 mL round bottomed flask benzyl 4-hydroxybenzoate (1.445 g, 6.33 mmol) and potassium carbonate (4.17 g, 30.1 mmol) in acetone (100 ml) were combined. Tert-butyl 2-bromoacetate (0.908 ml, 6.03 mmol) was added dropwise. The solution was stirred at 65° C. overnight. The solution was cooled then, the reaction mixture was filtered through a sintered glass funnel. The filtrate was concentrated to afford pale yellow oil, which was purified via silica gel chromatography (40 g, 30% EtOAc:Heptane) to afford benzyl 4-(2-tert-butoxy-2-oxoethoxy)benzoate (2.06 g, 5.90 mmol, 98% yield) as colorless oil. LC/MS (Table 1, Method a) Rt=4.31 min.

Workup

  1. temperatureThe solution was cooled
  2. filtrationthe reaction mixture was filtered through a sintered glass funnel
  3. concentrationThe filtrate was concentrated
  4. customto afford pale yellow oil, which
  5. customwas purified via silica gel chromatography (40 g, 30% EtOAc:Heptane)

Sources & evidence

ORD record
ord-19f1f934b8ae425da13920920e379db8
Source dataset
uspto-grants-2010_11
Patent number
US07834039B2

Reaction notes

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