Acetone → HCID 21427785, compound

HRID 437269Notes

Reaction equation

HRID 437269 reaction equation
[CH3:1][C:2]([OH:11])([CH3:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH2:9].[CH3:12][C:13]([CH3:15])=O>C1C=CC=CC=1>[CH3:12][C:13]1([CH3:15])[O:11][C:2]([CH3:1])([CH3:10])[C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[NH:9]1

Participants

4

Reactant 2

HCID 180AcetoneHCID 2535272-(2-aminophenyl)propan-2-ol

Product 1

HCID 21427785HCID 21427785, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 15 g (0.1 mol) α,α-dimethyl-2-aminobenzyl alcohol and 5.7 g (0.1 mol) acetone in 120 ml of benzene was heated under reflux in a Dean-Stark trap for 3 hours. About 1.5 ml of water was separated from the reaction mixture. The benzene solution was then evaporated to give an oil which solidified on standing. Recrystallization from ethanol-water gave 5.2 g 2,2,4,4-tetramethyl-1,2-dihydro-4H-3,1-benzoxazine, as a white solid.

Workup

  1. temperatureunder reflux in a Dean-Stark trap for 3 hours
  2. customAbout 1.5 ml of water was separated from the reaction mixture
  3. customThe benzene solution was then evaporated
  4. customto give an oil which
  5. customRecrystallization from ethanol-water

Sources & evidence

ORD record
ord-b6c8389db47b4922bf9498fc5ddefe47
Source dataset
uspto-grants-1977_06
Patent number
US04030906

Reaction notes

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