Ethylene Glycol → HCID 23294926, compound

HRID 1955283Notes

Reaction equation

[C:1]1([C:7]2([CH2:15]C#N)[CH2:12][CH2:11][CH2:10][C:9]([CH3:14])([CH3:13])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:18].[K+].C(O)C[OH:22]>>[C:1]1([C:7]2([C:15]([OH:22])=[O:18])[CH2:12][CH2:11][CH2:10][C:9]([CH3:14])([CH3:13])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 3

HCID 174Ethylene Glycol

HCID 14797Potassium Hydroxide

HCID 23295004HCID 23295004, compound

Product 1

HCID 23294926HCID 23294926, compoundYield 27%

Procedure

NaH (60% dispersion in mineral oil, 72.3 mmol) was washed several times with n-hexane and suspended in DMF. A mixture of phenylacetonitrile (24.1 mmol) and de-O-p-toluene-sulfonyl-2,2-dimethyl-1,5-pentanediol (24.1 mmol) in DMF was added dropwise. The reaction mixture was stirred at 70° C. for 3 h and DMF was evaporated under reduced pressure. Excess hydride was then decomposed by the cautious addition of H2O. Extraction with Et2O, drying of the organic layer (MgSO4) and evaporation of the solvent afforded 1-phenyl-3,3-dimethylcyclohexaneacetonitrile that was chromatographed on silica using petroleumether-EtOAc 98:2 as eluent; 1H NMR (CDCl3) δ 0.96 (s, 3H), 1.26 (m, 1H), 1.31 (m, 3H) 1.59 (m, 2H), 1.78 (m, 2H), 1.92 (m, 2H), 2.23 (m, 1H), 7.49 (m, 5H). 7.0 mmol of the nitrile was refluxed with KOH (40%, 15 mL) in ethyleneglycol (40 mL) for two days. It was then allowed to cool to room temperature and was extracted with Et2O. The aqueous layer was acidified and extracted with Et2O. The organic layer was dried (MgSO4) and concentrated to provide 1.5 g (27%) of the desired carboxylic acid.

Workup

customwas chromatographed on silica
extractionwas extracted with Et2O
extractionextracted with Et2O
dry with materialThe organic layer was dried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-81cae226594447e887805a164eec7a3a
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06124354

Reaction notes

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