Reaction #1929032

ord-694bff5dd88b45c78e7ec4c0d298228d

Reaction equation

O.O.[Na+].[Na+].[O]=[Cr](=[O])([O-])[O][Cr](=[O])(=[O])[O-]
sodium dichromate dihydrate
CCOCC
ether
CCCCCCCCCCC(O)CBr
1-bromo-2-dodecanol
→
CCCCCCCCCCC(=O)CBr
1-bromo-2-dodecanone
Yield 80.0%

Reactants

O.O.[Na+].[Na+].[O]=[Cr](=[O])([O-])[O][Cr](=[O])(=[O])[O-]
sodium dichromate dihydrate
CCOCC
ether
CCCCCCCCCCC(O)CBr
1-bromo-2-dodecanol

Reagents

None

Solvents

O
water
O=S(=O)(O)O
sulfuric acid
CC(C)=O
acetone

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherA solution obtained in advance
  2. 2
    workup.ADDITIONwas dropped
  3. 3
    Otherthe solvent was removed
  4. 4
    OtherAs a result, a white solid was obtained

Procedure

In a 1000 ml eggplant-shaped flask, 14 g of 1-bromo-2-dodecanol was dissolved in 110 ml of acetone. A solution obtained in advance by dissolving 35 g of sodium dichromate dihydrate in 150 ml of distilled water and 25 ml of sulfuric acid was dropped thereto. These substances were stirred at room temperature for 1.5 hours, and then 250 ml of ether was added thereto. The resultant substance was dehydrated, and the solvent was removed. As a result, a white solid was obtained. The yield was 80%.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08945769B2uspto-grants-2015_02