Ethylene Glycol → HCID 57656447, compound

HRID 911602Notes

Reaction equation

HRID 911602 reaction equation
[CH3:1][C:2]([CH3:16])([CH3:15])[CH2:3][CH2:4][C:5]([C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=1)=[O:6].[CH2:17](O)[CH2:18][OH:19].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.CCOC(C)=O>[CH3:1][C:2]([CH3:16])([CH3:15])[CH2:3][CH2:4][C:5]1([C:7]2[CH:8]=[CH:9][C:10]([C:11]#[N:12])=[CH:13][CH:14]=2)[O:19][CH2:18][CH2:17][O:6]1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 57656460HCID 57656460, compound

Product 1

HCID 57656447HCID 57656447, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
135 °C

Procedure

Dissolve 4-(4,4-dimethyl-pentanoyl)-benzonitrile (275 mg, 1.28 mmol) in toluene (10 mL). Add ethylene glycol (0.35 mL, 6.4 mmol) and p-toluenesulfonic acid monohydrate (24 mg, 0.128 mmol). Heat the mixture at 135° C. in a Dean-Stark for 2 h and then at 120° C. overnight. Cool the mixture to room temperature, dilute with EtOAc and wash with saturated aqueous NaHCO3. Dry the organic phase over MgSO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on basic alumina eluting with hexane and hexane/EtOAc (19:1) to give the desired intermediate as an oil (0.272 g, 82%).

Workup

  1. customat 120° C.
  2. customovernight
  3. temperatureCool the mixture to room temperature
  4. washwash with saturated aqueous NaHCO3
  5. dry with materialDry the organic phase over MgSO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customPurify the crude mixture by chromatography on basic alumina eluting with hexane and hexane/EtOAc (19:1)

Sources & evidence

ORD record
ord-0d7f373b0b2b4dd3965fc64d9fdb8753
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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