Potassium Carbonate → HCID 69990966, compound

HRID 1250104Notes

Reaction equation

HRID 1250104 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].C(=O)([O-])[O-].[K+].[K+].[OH:16][CH2:17]/[CH:18]=[CH:19]/[C:20]1[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=1>CC(C)=O>[C:6]([O:5][C:3](=[O:4])[CH2:2][O:26][C:22]1[CH:23]=[CH:24][CH:25]=[C:20](/[CH:19]=[CH:18]/[CH2:17][OH:16])[CH:21]=1)([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 12641156HCID 12641156, compound

Product 1

HCID 69990966HCID 69990966, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of tert-butyl bromoacetate (0.60 mL, 4.03 mmol) and potassium carbonate (1.12 g, 8.06 mmol) was added to a solution of trans-3-(3-hydroxypropenyl)phenol (0.58 g, 3.84 mmol) in acetone (15 mL) at room temperature under a nitrogen atmosphere and stirred for about 20 hours. The mixture was filtered, and the filtrate was concentrated to dryness. Purification by flash chromatography, eluting with hexane/ethyl acetate, gave pure trans-[3-(3-hydroxypropenyl)phenoxy]acetic acid tert-butyl ester as a clear oil (0.987 g, 97%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated to dryness
  3. customPurification by flash chromatography
  4. washeluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-91aaa4f56e3a47a29271282c632ca777
Source dataset
uspto-grants-2002_01
Patent number
US06335459B1

Reaction notes

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