tert-Butanol → HCID 67108500, compound

HRID 471882

Reaction equation

HRID 471882 reaction equation
[CH2:1]([O:3][C:4]([C:6]1(CC=C)[CH2:11][CH2:10][CH2:9][CH:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:7]1)=[O:5])[CH3:2].C(=O)([O-])[O-:21].[K+].[K+].N12CCC(CC1)CC2.S([O-])([O-])=O.[Na+].[Na+].[C:40]([OH:44])(C)([CH3:42])[CH3:41]>O.[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+]>[CH2:1]([O:3][C:4]([C:6]1([CH2:41][CH:40]([OH:44])[CH2:42][OH:21])[CH2:11][CH2:10][CH2:9][CH:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:7]1)=[O:5])[CH3:2]

Participants

8

Reactant 5

HCID 6386tert-ButanolHCID 7527QuinuclidineHCID 11430Potassium CarbonateHCID 24437Sodium SulfiteHCID 67108610HCID 67108610, compound

Product 1

HCID 67108500HCID 67108500, compound

Reagents, catalysts & solvents 2

HCID 178511488HCID 178511488, compoundCatalystHCID 962WaterSolvent

Procedure

To a solution of 1-allyl-cyclohexane-1,3-dicarboxylic acid diethyl ester from step 2 (250 g, 0.93 mol) in t-butanol (2.3 L) and water (2.3 L) was added potassium ferricyanide (920 g, 2.79 mol), potassium carbonate (386 g, 2.79 mol), potassium osmate dihydrate (4.75 g, 13 mmol) and quinuclidine (0.073 g, 7.0 mmol). The resulting dark colored solution was stirred at rt overnight and then quenched with portion-wise addition of sodium sulfite (1.05 kg, 8.37 mol). After dilution with ethyl acetate, it was extracted, washed with water and brine, dried over Na2SO4, and concentrated under reduced pressure. The resulting residue (224 g) was used in the next step without delay and without further purification.

Workup

  1. extractionAfter dilution with ethyl acetate, it was extracted
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue (224 g) was used in the next step without delay and without further purification

Sources & evidence

ORD record
ord-7468b90972ee44d690b9f8ca57c7a586
Source dataset
uspto-grants-2014_01
Patent number
US08633190B2

Linked notes

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