Hydrochloric Acid → HCID 22324252, compound

HRID 1756688Notes

Reaction equation

HRID 1756688 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[C:8]([OH:10])=[O:9])([CH3:4])[CH3:3].[H-].[Na+].[CH3:21]I.Cl>O1CCCC1.CN(C)C=O.O>[CH3:4][C:2]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[O:14][CH3:21])[C:8]([OH:10])=[O:9])([CH3:1])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 150073,5-Di-tert-butyl-4-hydroxybenzoic acidHCID 24758Sodium hydride3×

Product 1

HCID 22324252HCID 22324252, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To 50 g {200 mmol) of 3,5-bis(1,1-dimethylethyl)-4-hydroxy benzoic acid dissolved in 1.1 liters of a 10/1 tetrahydrofuran/dimethylformamide solution were added 24.0 g of a sodium hydride dispersion (60%, by weight, sodium hydride dispersed in mineral oil). The sodium hydride dispersion was added portionwise at a rate such that the reaction solution temperature was kept below 35° C. The resulting solution was stirred for 19 hours and then 28.4 g (220 mmol) of methyl iodide were added. The resulting solution was stirred for 22 hours and then 25 ml of water were added to quench the reaction. Four hundred milliliters of a 1N hydrochloric acid solution were then added in order to acidify the quenched solution. The acidic solution was then concentrated and extracted three times with ethyl acetate. The ethyl acetate extracts were combined, washed three times with water and once with a saturated brine solution and then concentrated to dryness to provide residue. This residue was crystallized from a hexane/methylene chloride solution to provide 34.62 of title product m.p. 192°-195° C.

Workup

  1. additionwere added
  2. customwas kept below 35° C
  3. stirringThe resulting solution was stirred for 22 hours
  4. customto quench
  5. customthe reaction
  6. concentrationThe acidic solution was then concentrated
  7. extractionextracted three times with ethyl acetate
  8. washwashed three times with water
  9. concentrationonce with a saturated brine solution and then concentrated to dryness
  10. customto provide residue
  11. customThis residue was crystallized from a hexane/methylene chloride solution

Sources & evidence

ORD record
ord-96f7ed4aa26e4ca397d72cef80460228
Source dataset
uspto-grants-1995_08
Patent number
US05441984

Reaction notes

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