Formaldehyde → HCID 21427782, compound

HRID 437268Notes

Reaction equation

HRID 437268 reaction equation
[CH2:1]=O.[CH3:3][C:4]([OH:13])([CH3:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH2:11]>O.C1C=CC=CC=1>[CH3:12][C:4]1([CH3:3])[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[NH:11][CH2:1][O:13]1

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 2535272-(2-aminophenyl)propan-2-ol

Product 1

HCID 21427782HCID 21427782, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

An 8.25-ml solution of 37% aqueous formaldehyde (0.099 mol) was added over 5 minutes to a cooled (0° C.) mixture of 10 g (0.066 mol) α,α-dimethyl-2-aminobenzyl alcohol in 50 ml water. The reaction mixture was then diluted with 50 ml benzene and vigorously stirred for 5 minutes. The aqueous layer was separated and extracted with benzene. The benzene layer of the reaction mixture and the benzene extracts were combined, dried over magnesium sulfate and evaporated. The resulting oil was distilled through a short column to give 6.3 g (b.p. 120° -125° C. at 0.1 mm of Hg) of 4,4-dimethyl-1,2-dihydro-4H-3,1-benzoxazine, as a colorless oil. Elemental analysis showed: %C, calc. 73.6, found 68.3: %H, calc. 8.0, found 7.6; %N, calc. 8.6, found 8.6.

Workup

  1. temperaturea cooled
  2. customThe aqueous layer was separated
  3. extractionextracted with benzene
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. distillationThe resulting oil was distilled through a short column

Sources & evidence

ORD record
ord-f74a9330c1e14953bd442e710e4f60d7
Source dataset
uspto-grants-1977_06
Patent number
US04030906

Reaction notes

Loading…