Methanol → HCID 20540214, compound

HRID 1065269Notes

Reaction equation

HRID 1065269 reaction equation
[NH2-].[Na+].CC1C=CC=CC=1.[C:10]1([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3(C#N)[CH2:33][CH2:32][C:27]4([O:31][CH2:30][CH2:29][O:28]4)[CH2:26][CH2:25]3)=[CH:20][CH:19]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CO>CC1C=CC=CC=1C>[C:10]1([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([CH:24]3[CH2:33][CH2:32][C:27]4([O:28][CH2:29][CH2:30][O:31]4)[CH2:26][CH2:25]3)=[CH:20][CH:19]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 1140TolueneHCID 24533Sodium amideHCID 15586330HCID 15586330, compound

Product 1

HCID 20540214HCID 20540214, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To a stirred and heated (±65° C.) mixture of 60 parts of sodium amide solution 50% in dimethylbenzene and 315 parts of methylbenzene are added portionwise 33.5 parts of 8-[4-(phenylmethoxy)phenyl]-1,4-dioxaspiro[4,5]decane-8-carbonitrile. Upon completion, stirring is continued for 24 hours at reflux. The reaction mixture is cooled, about 16 parts of methanol are added dropwise and the whole is poured onto ice-water. The product is extracted with trichloromethane. The extract is dried, filtered and evaporated, yielding 27 parts (87%) of 8-[4-(phenylmethoxy)phenyl]-1,4-dioxaspiro[4,5]decane as a residue.

Workup

  1. temperatureheated
  2. stirringUpon completion, stirring
  3. temperatureat reflux
  4. additionare added dropwise
  5. additionthe whole is poured onto ice-water
  6. extractionThe product is extracted with trichloromethane
  7. customThe extract is dried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-2fc25c90e7114986aa683be42b854a37
Source dataset
uspto-grants-1982_05
Patent number
US04329353

Reaction notes

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