Hydrochloric Acid → HCID 21107216, compound

HRID 2377358Notes

Reaction equation

HRID 2377358 reaction equation
[Br:1][C:2]1(C=O)[CH:11]=[CH:10][C:9]2[O:8][C:7]([CH3:13])([CH3:12])[CH2:6][C:5]([CH3:15])([CH3:14])[C:4]=2[CH2:3]1.CC(=CC)C.Cl([O-])=O.[Na+].[OH-:27].[Na+].Cl.C[C:31]([OH:34])(C)C>O.C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:31]([OH:34])=[O:27])[CH:11]=1)[O:8][C:7]([CH3:12])([CH3:13])[CH2:6][C:5]2([CH3:14])[CH3:15]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 6386tert-ButanolHCID 105532-Methyl-2-buteneHCID 14798Sodium HydroxideHCID 21107215HCID 21107215, compoundHCID 23668197Sodium Chlorite

Product 1

HCID 21107216HCID 21107216, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A stirred, cooled (ice bath) solution of 6-bromo-2,2,4,4-tetramethylchroman-6-carbaldehyde (U.S. Pat. No. 6,303,785 incorporated herein by reference; 3.31 g, 11.15 mmol) in 2-methyl-2-propanol (30 mL) was treated with glacial acetic acid (30 mL) followed by 2-methyl-2-butene (12 mL, 111.5 mmol). A solution of sodium chlorite (2.15 g, 18.95 mmol) in water (15 mL) was added dropwise to the reaction mixture. The reaction mixture was then allowed to gradually warm up to ambient temperature and stirred for 4 h at the end of which it was made basic 2N sodium hydroxide solution and then acidified with 2N hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title product as a yellow solid (3.23 g, 93%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-e0a294d8e2d145229d644fcce0f87fc4
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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