Acetone → HCID 70510756, compound

HRID 894639Notes

Reaction equation

HRID 894639 reaction equation
[OH:1][C@H:2]1[CH2:15][C@@H:14]([O:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)[C@H:13](/[CH:23]=[CH:24]/[CH:25]([O:32][CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][O:34]2)[CH2:26][CH2:27][CH:28]=[C:29]([CH3:31])[CH3:30])[C@H:3]1[CH2:4]/[CH:5]=[CH:6]\[CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11].CC(C)=O.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C>CCOCC>[CH3:30][C:29]([CH3:31])=[CH:28][CH2:27][CH2:26][CH:25]([O:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][O:34]1)/[CH:24]=[CH:23]/[C@@H:13]1[C@@H:3]([CH2:4]/[CH:5]=[CH:6]\[CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])[C:2](=[O:1])[CH2:15][C@H:14]1[O:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][O:18]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 3776IsopropanolHCID 70509004HCID 70509004, compoundHCID 131709961Jones' reagent

Product 1

HCID 70510756HCID 70510756, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

At -20°, a solution of 2.6 g. of the alcohol obtained according to (d) in 33 ml. of acetone was combined with 2.72 ml. of Jones reagent and stirred for 30 minutes at this temperature. Thereafter, 3.3 ml. of isopropanol was added dropwise thereto, the mixture was stirred for another 10 minutes at -20°, diluted with ether, and washed three times with water. The organic phase was dried over magnesium sulfate and concentrated under vacuum, thus obtaining 2 g. of the title compound.

Workup

  1. customAt -20°
  2. washwashed three times with water
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customthus obtaining 2 g

Sources & evidence

ORD record
ord-8382d755e58d47b4abf162679c8e3583
Source dataset
uspto-grants-1981_08
Patent number
US04284646

Reaction notes

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