Sodium Bromide → HCID 86687809, compound

HRID 716489Notes

Reaction equation

HRID 716489 reaction equation
[Na+].[Br-].C([O-])(O)=O.[Na+].[C:8]1([CH2:14]/[C:15](/[CH3:19])=[CH:16]/[CH2:17][OH:18])[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]=1.[O-]Cl.[Na+]>C1(C)C=CC=CC=1.O>[C:8]1([CH2:14]/[C:15](/[CH3:19])=[CH:16]/[CH:17]=[O:18])[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]=1

Participants

7

Reactant 4

HCID 253881Sodium BromideHCID 516892Sodium BicarbonateHCID 23665760Sodium HypochloriteHCID 66584185HCID 66584185, compound

Product 1

HCID 86687809HCID 86687809, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

NaBr (0.6 g, 0.006 mol) and NaHCO3 (6.4 g, 0.076 mol) were mixed together with water (60 ml), toluene (250 g) and (2E)-4-cyclohexenyl-3-methylbut-2-en-1-ol (96 g (0.573 mol, purity: 99% sum of the isomers) at room temperature with continuous stirring. NaOCl (13% w/w aqueous 426.8 g, 0.745 mol) was added to the reaction mass over 2 h. Stirring was continued for another 1 h. The aqueous phase was removed, organic phase was washed with a solution of NaHCO3 and then with water. The organic phase thus obtained was concentrated and crude product purified by fractional distillation to provide (2E)-4-cyclohexenyl-3-methylbut-2-enal (62.6 g, yield: 66%, GC purity: 95% sum of the isomers).

Workup

  1. customThe aqueous phase was removed
  2. washorganic phase was washed with a solution of NaHCO3
  3. customThe organic phase thus obtained
  4. concentrationwas concentrated
  5. distillationcrude product purified by fractional distillation

Sources & evidence

ORD record
ord-46a90948d00342afba4ce61203a0135d
Source dataset
uspto-grants-2015_11
Patent number
US09187709B2

Reaction notes

Loading…