Ethylene Glycol → HCID 15586330, compound

HRID 1065263Notes

Reaction equation

HRID 1065263 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][C:5]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:12][CH:11]=2)([C:8]#[N:9])[CH2:4][CH2:3]1.[CH2:24](O)[CH2:25][OH:26].CC1C=CC(S(O)(=O)=O)=CC=1.CC1C=CC=CC=1>O>[C:18]1([CH2:17][O:16][C:13]2[CH:14]=[CH:15][C:10]([C:5]3([C:8]#[N:9])[CH2:6][CH2:7][C:2]4([O:26][CH2:25][CH2:24][O:1]4)[CH2:3][CH2:4]3)=[CH:11][CH:12]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 20540232HCID 20540232, compound

Product 1

HCID 15586330HCID 15586330, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 65 parts of 4-oxo-1-[4-(phenylmethoxy)phenyl]-1-cyclohexanecarbonitrile, 15.7 parts of 1,2-ethanediol, 0.2 parts of 4-methylbenzenesulfonic acid and 360 parts of methylbenzene is stirred and refluxed overnight with water-separator. The reaction mixture is cooled, washed successively with water, with a sodium hydroxide solution 5% and again with water, dried, filtered and evaporated. The residue is crystallized from 2-propanol, yielding 33.5 parts (47%) of 8-[4-(phenylmethoxy)phenyl]-1,4-dioxaspiro[4,5]decane-8-carbonitrile.

Workup

  1. temperatureThe reaction mixture is cooled
  2. washwashed successively with water, with a sodium hydroxide solution 5% and again with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is crystallized from 2-propanol

Sources & evidence

ORD record
ord-7f5f7b648d794e73b873d9f1af68380a
Source dataset
uspto-grants-1982_05
Patent number
US04329353

Reaction notes

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