tert-Butanol → 1-(2,3-Dihydroxy-propyl)-cyclohexane-1,3-dicarboxylic acid diethyl ester

HRID 2199448Notes

Reaction equation

HRID 2199448 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].[K].C(=O)([O-])[O-:22].[K+].[K+].N12CCC(CC1)CC2.S([O-])([O-])=O.[Na+].[Na+].[C:41]([OH:45])(C)([CH3:43])[CH3:42]>O>[CH2:1]([O:3][C:4]([C:6]1([CH2:42][CH:41]([OH:45])[CH2:43][OH:22])[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 6

HCID 6386tert-ButanolHCID 7527QuinuclidineHCID 11430Potassium CarbonateHCID 24437Sodium SulfiteHCID 5462222PotassiumHCID 671086101-Allyl-cyclohexane-1,3-dicarboxylic acid diethyl ester

Product 1

HCID 671085001-(2,3-Dihydroxy-propyl)-cyclohexane-1,3-dicarboxylic acid diethyl ester

Reagents, catalysts & solvents 1

HCID 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 ferricyanade (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-d82b2c062411451e83c887d84dd9ff66
Source dataset
uspto-grants-2016_06
Patent number
US09359297B2

Reaction notes

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