2-Bromoethanol → HCID 10730396, compound

HRID 1109309Notes

Reaction equation

HRID 1109309 reaction equation
[OH:1][NH:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][CH:5]=1.[OH-].[Na+].Br[CH2:20][CH2:21][OH:22]>C(O)C.O>[OH:22][CH2:21][CH2:20][O:1][NH:2][C:3](=[O:16])[C:4]1[CH:5]=[CH:6][C:7]([C:10](=[O:15])[C:11]([CH3:13])([CH3:12])[CH3:14])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 108982-BromoethanolHCID 14798Sodium HydroxideHCID 10799007HCID 10799007, compound

Product 1

HCID 10730396HCID 10730396, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 4.0 grams (18.1 mmol) of N-hydroxy-4-pivaloylbenzamide in 10 milliliters of ethanol is added an aqueous solution of 725 milligrams (18.1 mmol) of sodium hydroxide in 1 milliliter of water. To this is added 1.67 milliliters (23.6 mmol) of 2-bromoethanol; and the resulting mixture is heated at 55° C. for 24 hours. The mixture is cooled to 20° C., concentrated, and extracted 3 times with 10 milliliters of chloroform. The combined extracts are washed with 15 milliliters of water and then 15 milliliters of brine, dried over magnesium sulfate and concentrated. The residue is recrystallized from methylene chloride/hexane (1:4) to yield N-(2-hydroxyethoxy)-4-pivaloylbenzamide.

Workup

  1. temperatureThe mixture is cooled to 20° C.
  2. concentrationconcentrated
  3. extractionextracted 3 times with 10 milliliters of chloroform
  4. washThe combined extracts are washed with 15 milliliters of water
  5. dry with material15 milliliters of brine, dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue is recrystallized from methylene chloride/hexane (1:4)

Sources & evidence

ORD record
ord-ab156d78a2bd488da46f9187465ee5f1
Source dataset
uspto-grants-1994_06
Patent number
US05319123

Reaction notes

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