3-Hydroxybenzyl alcohol → 2-[3-(Hydroxymethyl)phenoxy]acetamide

HRID 594992Notes

Reaction equation

HRID 594992 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].Br[CH2:11][C:12]([NH2:14])=[O:13].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:6][CH2:5][C:4]1[CH:3]=[C:2]([CH:9]=[CH:8][CH:7]=1)[O:1][CH2:11][C:12]([NH2:14])=[O:13]

Participants

5

Reactant 3

HCID 1023-Hydroxybenzyl alcoholHCID 11430Potassium CarbonateHCID 696322-Bromoacetamide

Product 1

HCID 9273882-[3-(Hydroxymethyl)phenoxy]acetamideYield 43%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-hydroxybenzyl alcohol (500 mg, 4 mmol) in acetonitrile (10 mL) was added 2-bromoacetamide (1 eq) and potassium carbonate (1 eq). The resulting suspension was stirred at rt for 18 h. The solvent was removed in vacuo and the residue partitioned between EtOAc and H2O. The aqueous layer was acidified with dilute HCl (2M) and then re-extracted with EtOAc (3×50 mL). The organic phases were combined, dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was purified by column chromatography (EtOAc: methanol) to give 2-(3-(hydroxymethyl)phenoxy)acetamide (320 mg, 43%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between EtOAc and H2O
  3. extractionre-extracted with EtOAc (3×50 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue was purified by column chromatography (EtOAc: methanol)

Sources & evidence

ORD record
ord-eecaca7346c444e6b2c0cd595518b658
Source dataset
uspto-grants-2016_01
Patent number
US09242987B2

Reaction notes

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