Bromoacetic Acid → HCID 19046549, compound

HRID 1781489Notes

Reaction equation

HRID 1781489 reaction equation
[CH:1]([C:4]1[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:7]=[C:6]([CH:13]([CH3:15])[CH3:14])[C:5]=1[OH:16])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:20][C:21]([OH:23])=[O:22]>O1CCCC1>[CH3:14][CH:13]([C:6]1[CH:7]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:9]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]=1[O:16][CH2:20][C:21]([OH:23])=[O:22])[CH3:15]

Participants

5

Reactant 3

HCID 6227Bromoacetic AcidHCID 24758Sodium hydrideHCID 821582,4,6-Triisopropylphenol

Product 1

HCID 19046549HCID 19046549, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 2,4,6-triisopropylphenol (4.0 g, 18 mmol) in 50 mL tetrahydrofuran was added dropwise to a suspension of sodium hydride (1.52 g, 38 mmol) in 25 mL tetrahydrofuran. The resulting pale green suspension was stirred for 30 minutes before a solution of bromoacetic acid (2.52 g, 18 mmol) in 50 mL tetrahydrofuran was added dropwise. The resulting thick suspension was stirred for 16 hours and then concentrated in vacuo. The residue was partitioned between 1N HCl and dichloromethane, the organic extract was dried over MgSO4, filtered, and concentrated to give a yellow solid. Recrystallized from hexanes to give 3.1 g of [2,4,6-tris(1-methylethyl)phenoxy]acetic acid, mp 105°-108° C.

Workup

  1. additionwas added dropwise
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between 1N HCl and dichloromethane
  4. extractionthe organic extract
  5. dry with materialwas dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a yellow solid
  9. customRecrystallized from hexanes

Sources & evidence

ORD record
ord-25e0b70a444549a7a273b565e9ce509e
Source dataset
uspto-grants-1997_05
Patent number
US05633287

Reaction notes

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