Hydrochloric Acid → HCID 10447662, compound

HRID 1029536Notes

Reaction equation

HRID 1029536 reaction equation
[C:1]1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:12][C:13]([C:16]1[CH:17]=[C:18]([CH2:27][CH2:28][C:29]([NH:31][NH2:32])=[O:30])[CH:19]=[C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:21]=1[OH:22])([CH3:15])[CH3:14].Cl>C(OCC)(OCC)OCC.C(OCC)(=O)C>[CH3:15][C:13]([C:16]1[CH:17]=[C:18]([CH2:27][CH2:28][C:29]2[O:30][CH:1]=[N:32][N:31]=2)[CH:19]=[C:20]([C:23]([CH3:24])([CH3:25])[CH3:26])[C:21]=1[OH:22])([CH3:12])[CH3:14]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 648653,5-Di-tert-butyl-4-hydroxyhydrocinnamic acid hydrazide

Product 1

HCID 10447662HCID 10447662, compoundYield 774.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31214Ethyl orthoformateSolvent

Procedure

A catalytic amount of p-toluenesulfonic acid (25 mg) is added to a stirring solution of 3,5-bis(1,1-dimethylethyl)-4-hydroxybenzenepropanoic acid hydrazide (0.50 g, 1.71 mmol) in triethyl orthoformate (10 mL). After 30 minutes, 10 mL of 1N hydrochloric acid is added, and stirring is continued for 30 minutes. The reaction mixture is diluted with ethyl acetate and washed twice with a saturated solution of sodium bicarbonate, twice with water, and once with brine. Drying the organic phase over magnesium sulfate and evaporation gives a crude product which is chromatographed on a column of silica with ethyl acetate/hexane (1/9 then 1/4) to afford 0.34 g (67%) of 2,6-bis(1,1-dimethylethyl)-4-[2-(1,3,4-oxadiazol-2-yl)ethyl]phenol, mp 100.0°-101.0° C.

Workup

  1. waitis continued for 30 minutes
  2. washwashed twice with a saturated solution of sodium bicarbonate, twice with water
  3. customDrying the organic phase
  4. customover magnesium sulfate and evaporation
  5. customgives a crude product which
  6. customis chromatographed on a column of silica with ethyl acetate/hexane (1/9

Sources & evidence

ORD record
ord-abf2a9f5881e4c1bb6a9a61cf65af418
Source dataset
uspto-grants-1992_04
Patent number
US05102897

Reaction notes

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