Hydrochloric Acid → HCID 59189493, compound

HRID 333475Notes

Reaction equation

HRID 333475 reaction equation
[C@]12(C)C(C)(C)C(CC1)CC2C([O:12][CH:13]([C:18]1[CH:23]=[CH:22][C:21]([I:24])=[CH:20][C:19]=1[N+:25]([O-:27])=[O:26])[C:14]([CH3:17])([CH3:16])[CH3:15])=O.C([O-])([O-])=O.[K+].[K+].O.Cl>CO>[I:24][C:21]1[CH:22]=[CH:23][C:18]([CH:13]([OH:12])[C:14]([CH3:15])([CH3:16])[CH3:17])=[C:19]([N+:25]([O-:27])=[O:26])[CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11430Potassium CarbonateHCID 86639081HCID 86639081, compound

Product 1

HCID 59189493HCID 59189493, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of single diastereomer (R or S)-1-(4-iodo-2-nitrophenyl)-2,2-dimethyl-1-propyl (1S)-camphanate (409 mg, 0.79 mmol) and K2CO3 (110 mg, 0.8 mmol) in methanol (15 mL) was heated to reflux for 30 minutes. Water (5 mL) was added and the solution was neutralized to pH 7 with 1M HCl. Solvent was removed in vacuo and the residue was taken into a mixture of ethyl acetate (30 mL) and water (10 mL). The organic phase was separated, dried over anhydrous Na2SO4, concentrated in vacuo, and purified by silica gel column chromatography to yield single enantiomer (R or S)-1-(4-iodo-2-nitrophenyl)-2,2-dimethyl-1-propanol (260 mg, 98%) as a light yellow oil. 1H NMR was identical to that of the racemic alcohol. The absolute configuration of the single enantiomer alcohol is not determined.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 30 minutes
  3. customSolvent was removed in vacuo
  4. additionthe residue was taken into a mixture of ethyl acetate (30 mL) and water (10 mL)
  5. customThe organic phase was separated
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo
  8. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-308debaa33634de09ebdd4011c0a52eb
Source dataset
uspto-grants-2014_11
Patent number
US08877905B2

Reaction notes

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