Hydrochloric Acid → HCID 58516557, compound

HRID 1468466Notes

Reaction equation

[CH3:1][C:2]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)([CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6])[CH3:3].[Na+].[I-:17].[OH-].[Na+].[O-]Cl.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+].Cl>CO>[I:17][C:11]1[CH:10]=[C:9]([C:2]([CH3:1])([CH2:4][C:5]([CH3:6])([CH3:7])[CH3:8])[CH3:3])[CH:14]=[CH:13][C:12]=1[OH:15]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 10.30 g (50.00 mmol) of 4-(2,4,4-trimethylpentan-2-yl)phenol in 125 mL of methanol at 0° C., add 7.48 g (50.00 mmol) of NaI and 2.00 g (50 mmol) of NaOH. To the resulting mixture add 86 mL of 5% aqueous NaOCl solution (commercial bleach) over a one hour period. Stir the resulting slurry for one more hour at 0° C. Then add 30 mL of aqueous 10% Na2S2O3 solution, and acidify the resulting reaction mixture with addition of dilute hydrochloric acid. Extract the resulting mixture with methylene chloride, wash the resulting organic layer with brine, and dry it over anhydrous magnesium sulfate. Remove volatiles and purify the resulting residue by flash chromatography on silica gel eluting with 5 volume percent (vol %) ethyl acetate in hexanes to yield 11.00 g (66%) of (P2) as a viscous oil.

Workup

customthe resulting reaction mixture
extractionExtract the resulting mixture with methylene chloride
washwash the resulting organic layer with brine
dry with materialdry it over anhydrous magnesium sulfate
customRemove volatiles and purify the resulting residue by flash chromatography on silica gel eluting with 5 volume percent (vol %) ethyl acetate in hexanes
customto yield 11.00 g (66%) of (P2) as a viscous oil

Sources & evidence

ORD record: ord-6b1bc84f442143d2a7b4cf240f6672f9
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000108B2

Reaction notes

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