Bromocresol Green → HCID 54415452, compound

HRID 1018168Notes

Reaction equation

HRID 1018168 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([CH3:28])=[CH:13][O:14][C:15](=[O:27])[CH2:16][CH2:17][C:18](=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CC1C(Br)=C(O)C(Br)=CC=1C1(C2C=C(Br)C(O)=C(Br)C=2C)OS(=O)(=O)C2C=CC=CC1=2.C([BH3-])#N.[Na+]>CO.Cl.CO>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([CH3:28])=[CH:13][O:14][C:15](=[O:27])[CH2:16][CH2:17][CH:18]([OH:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 6451Bromocresol GreenHCID 5003444Sodium cyanoborohydrideHCID 541554244-Oxo-undecanoic Acid 3-(4-tert-butyl-phenyl)-2-methyl-propenyl Ester

Product 1

HCID 54415452HCID 54415452, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 21893726Hydrochloride methanolCatalystHCID 887MethanolSolvent

Procedure

A solution of 10.00 g 4-oxo-undecanoic acid 3-(4-tert-butyl-phenyl)-2-methyl-propenyl ester was dissolved in 60 ml methanol and a trace of bromocresol green was added. When 1.63 g sodium cyanoborohydride was added, the color changed immediately from yellow to deep blue. Several drops of 2N HCl/methanol solution turned the color of the reaction back to yellow. The reaction was stirred for 2½ hours, with occasional addition of acid to maintain the yellow color. The reaction mixture was evaporated to dryness and water was added to the residue. This solution was extracted with ether and washed with water. The solution was dried, filtered and evaporated to dryness to yield 10.07 g of a colorless oil.

Workup

  1. customthe color of the reaction back to yellow
  2. temperatureto maintain the yellow color
  3. customThe reaction mixture was evaporated to dryness and water
  4. additionwas added to the residue
  5. extractionThis solution was extracted with ether
  6. washwashed with water
  7. customThe solution was dried
  8. filtrationfiltered
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-a576ee1c10754d9183fe8385ea3c1902
Source dataset
uspto-grants-2002_11
Patent number
US06479682B1

Reaction notes

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