Formaldehyde → Benzoxazines

HRID 351948Notes

Reaction equation

HRID 351948 reaction equation
CO[C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[NH2:10][CH2:11][CH2:12]CO.C=O.C(N(CC)CC)C.C(Cl)(=O)C=C>O.C1(C)C=CC=CC=1>[O:9]1[C:6]2[CH:5]=[CH:4][CH:3]=[CH:8][C:7]=2[CH:12]=[CH:11][NH:10]1

Participants

8

Reactant 5

HCID 712FormaldehydeHCID 8471TriethylamineHCID 90154-MethoxyphenolHCID 90863-Amino-1-propanolHCID 13140Acryloyl chloride

Product 1

HCID 17845026BenzoxazinesYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A 500 mL flask was charged with 4-methoxyphenol (12.4 g, 100 mmol), 3-amino-1-propanol (7.5 g, 100 mmol), and paraformaldehyde (6.4 g, 213 mmol). Toluene (200 g) was added to the flask and the mixture was heated to reflux for one hour, during which time 3.8 mL of water was collected in a Dean-Stark trap. The solution was cooled to 0° C., and triethylamine (23 g, 227 mmol) was added to the flask. This was followed by the drop-wise addition of acryloyl chloride (11 g, 125 mmol). The solution was allowed to stir overnight at room temperature. The product was worked up in a similar fashion as described in previous examples. About 20 g (72% yield) of a low viscosity, orange liquid was recovered.

Workup

  1. temperaturethe mixture was heated
  2. customwas collected in a Dean-Stark trap
  3. customAbout 20 g (72% yield) of a low viscosity, orange liquid was recovered

Sources & evidence

ORD record
ord-f92f6734f97c4b21b95d511b32027356
Source dataset
uspto-grants-2004_06
Patent number
US06743852B2

Reaction notes

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