Toluene → HCID 20470935, compound

HRID 1388355Notes

Reaction equation

HRID 1388355 reaction equation
[CH3:1][N:2]1[CH2:8][C:7]2([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=3)[CH:4]([CH2:5][C:6]2=[O:17])[CH2:3]1.[CH3:18][C:19]([CH3:24])([CH2:22]O)[CH2:20][OH:21].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>CCOCC>[CH3:16][O:15][C:11]1[CH:10]=[C:9]([C:7]23[C:6]4([O:21][CH2:20][C:19]([CH3:24])([CH3:22])[CH2:18][O:17]4)[CH2:5][CH:4]2[CH2:3][N:2]([CH3:1])[CH2:8]3)[CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 31344Neopentyl glycolHCID 202650395-(3-Methoxyphenyl)-3-methyl-3-azabicyclo[3.2.0]heptan-6-one

Product 1

HCID 20470935HCID 20470935, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1.18 g. of 3-methyl-5-(m-methoxyphenyl)-3-azabicyclo[3.2.0]heptan-6-one, 0.78 g. of 2,2-dimethyl-1,3-propanediol and 1.05 g. of p-toluenesulfonic acid in 25 ml. of toluene was heated at reflux under a Dean-Stark trap for 29 hours. The mixture was cooled, diluted with ether, washed with 10% sodium hydroxide, and then with water giving a brown oil. This oil was distilled in a Kugelrohr apparatus at 175° C. and 0.10 mm., giving the desired product as a colorless oil.

Workup

  1. additionA mixture of 1.18 g
  2. temperatureat reflux under a Dean-Stark trap for 29 hours
  3. temperatureThe mixture was cooled
  4. washwashed with 10% sodium hydroxide
  5. distillationThis oil was distilled in a Kugelrohr apparatus at 175° C.

Sources & evidence

ORD record
ord-530e5b151c1c4f1cb5e4fd4f99bfc09f
Source dataset
uspto-grants-1984_02
Patent number
US04431661

Reaction notes

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