Water → HCID 20431223, compound
Reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([OH:23])[CH:12]([CH3:22])[CH2:13][N:14]2[CH2:19][CH:18]([CH3:20])[O:17][CH:16]([CH3:21])[CH2:15]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Na+].[C:27](OC(=O)C)(=[O:29])[CH3:28]>>[C:27]([O:23][CH:11]([C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:10][CH:9]=1)[CH:12]([CH3:22])[CH2:13][N:14]1[CH2:15][CH:16]([CH3:21])[O:17][CH:18]([CH3:20])[CH2:19]1)(=[O:29])[CH3:28]Participants
Procedure
7.2 g (0.02 mole) of 1-(p-tert.-butyl-phenyl)-2-methyl-3-(2,6-dimethylmorpholin-4-yl)-1-propanol (obtained according to Example 2) were stirred in 50 ml of acetic anhydride to room temperature for 3 hours. The reaction mixture was then introduced into 100 ml of water and the mixture was adjusted to a pH value of 7 with dilute sodium hydroxide solution and extracted with chloroform. The organic phase was dried over sodium sulphate and concentrated. The oily residue was taken up in ethyl acetate, the ethyl acetate mixture was shaken with active charcoal and filtered and the filtrate was concentrated. The resulting oil was digested with petroleium ether, a brown precipitate was separated off and the mixture was concentrated. 5.3 g (73% of theory) of 1-acetoxy-1-(p-tert.-butyl-phenyl)-2-methyl-3-(2,6-dimethylmorpholin-4-yl)-propane were obtained as a viscous oil.
Workup
- extractionextracted with chloroform
- dry with materialThe organic phase was dried over sodium sulphate
- concentrationconcentrated
- filtrationfiltered
- concentrationthe filtrate was concentrated
- customa brown precipitate was separated off
- concentrationthe mixture was concentrated
Sources & evidence
- ORD record
- ord-35d4014067234cae80afe574353773c5
- Source dataset
- uspto-grants-1985_01
- Patent number
- US04495184
Reaction notes
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