Water → HCID 69885815, compound

HRID 840068Notes

Reaction equation

HRID 840068 reaction equation
[Br:1][C:2]1([Br:14])[CH2:4][C:3]1([Br:13])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12].[OH2:15]>C(O)(=O)C.[O-2].[O-2].[O-2].[Cr+6]>[Br:1][C:2]1([Br:14])[CH2:4][C:3]1([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:15])=[O:12])[Br:13]

Participants

5

Reactant 2

HCID 962WaterHCID 18548200HCID 18548200, compound

Product 1

HCID 69885815HCID 69885815, compound

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 176Acetic AcidSolvent2×

Procedure

1,1,2-Tribromo-2-(7-hydroxyheptyl)cyclopropane (0.90 g, 2.3 mmol) was dissolved in 60 ml of glacial acetic acid. A solution of 1.0 g (10 mmol) of chromium trioxide dissolved in 14 ml of 90% aqueous acetic acid was added and the reaction mixture was stirred at room temperature for 24 hours. Water (300 ml) was added. The solution was extracted with ether. The ether phase was extracted three times with 1N NaOH solution. A little sodium bisulfite was added. The aqueous extracts were acidified with 6N HCl, and extracted with ether twice. The ether extracts were washed with brine, dried over magnesium sulfate and stripped to give 0.56 g 7-(1,1,2-tribromo-cyclopropyl)-heptanoic acid.

Workup

  1. additionwas added
  2. extractionThe solution was extracted with ether
  3. extractionThe ether phase was extracted three times with 1N NaOH solution
  4. additionA little sodium bisulfite was added
  5. extractionextracted with ether twice
  6. washThe ether extracts were washed with brine
  7. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-cc2b2c45c4a94b9a9ea4d39b1dcc6d3d
Source dataset
uspto-grants-2002_04
Patent number
US06365549B2

Reaction notes

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