Sulfuric Acid → 11-bromoundec-10-ynoic Acid

HRID 1388232

Reaction equation

HRID 1388232 reaction equation
[C:1]([OH:13])(=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[CH:11].[Br:14][O-].[Na+].Br[O-].BrBr.OS(O)(=O)=O>[OH-].[Na+]>[Br:14][C:11]#[C:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([OH:13])=[O:12]

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 24408BromineHCID 3103910-Undecynoic acidHCID 5460626HypobromiteHCID 23673712Sodium hypobromite

Product 1

HCID 411287611-bromoundec-10-ynoic Acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

To a solution of 36.45 g (200 mmol) of 10-undecynoic acid in 200 ml 1 N NaOH at 0° C. was added a solution of alkaline sodium hypobromite dropwise over 30 minutes, maintaining the temperature below 5° C. (the hypobromite solution was prepared by the dropwise addition of 35.16 g (220 mmol) of bromine to 55 ml of 20 N NaOH at 0°-5° C.). The mixture was stirred four hours at 0°-5° C., and was then acidified to PH 1 with 9 M H2SO4. The solution was extracted with three 150 ml portions of ether. The combined extracts were dried (Na2SO4) and evaporated yielding 50.159 (96% crude) of a pale yellow solid. THis was used without further purification.

Workup

  1. extractionThe solution was extracted with three 150 ml portions of ether
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. customevaporated
  4. customyielding 50.159 (96% crude) of a pale yellow solid
  5. customTHis was used without further purification

Sources & evidence

ORD record
ord-8651c3f7979f4deea05b1bb0ea1e24ce
Source dataset
uspto-grants-1984_02
Patent number
US04431263

Linked notes

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