Formaldehyde → N-(Hydroxymethyl)phenylacetamide

HRID 2427925Notes

Reaction equation

HRID 2427925 reaction equation
[C:1]1([CH2:7][C:8]([NH2:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:11]=[O:12]>C(=O)([O-])[O-].[K+].[K+]>[OH:12][CH2:11][NH:10][C:8](=[O:9])[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 7680Benzeneacetamide

Product 1

HCID 138717N-(Hydroxymethyl)phenylacetamideYield 44.4%

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateCatalyst

Procedure

A mixture of phenylacetamide 12 (2 g, 15 mmol) in a solution of potassium carbonate (4%, 2 ml, 0.6 mmol) and an aqueous solution of formaldehyde (37%, 2 ml, 20 mmol) was refluxed for 15 min (until completely dissolved). The mixture was cooled and extracted with CH2Cl2 (2×30 ml). The combined organic phases were dried over MgSO4 and were concentrated under reduced pressure to give a crude product (1.35 g), recrystallization in toluene (20 ml) gave N-hydroxymethylphenylacetamide 11 (1.1 g, 44%) in the form of a white powder. M.p. 78° C. 1H NMR (CDCl3, 300 MHz) δ 7.50-7.20 (m, 5H), 6.48 (br s, NH), 4.69 (t, J=7.0 Hz, 2H), 3.67 (t, J=7 Hz, OH), 3.60 (s, 2H). 13C NMR (CDCl3, 75 MHz) δ 172.9, 134.4, 129.5, 129.0, 127.5, 64.2, 43.6.

Workup

  1. dissolutionuntil completely dissolved)
  2. temperatureThe mixture was cooled
  3. extractionextracted with CH2Cl2 (2×30 ml)
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. concentrationwere concentrated under reduced pressure
  6. customto give
  7. customa crude product (1.35 g), recrystallization in toluene (20 ml)

Sources & evidence

ORD record
ord-9beed3ec75f04d538e87fc4ff7e16c0c
Source dataset
uspto-grants-2011_06
Patent number
US07968735B2

Reaction notes

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