Toluene → HCID 9840004, compound

HRID 1029534Notes

Reaction equation

HRID 1029534 reaction equation
[C:1](Cl)(Cl)=[O:2].C1(C)C=CC=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].C(=O)(O)[O-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:26][C:23]([C:20]1[CH:19]=[C:18]([CH2:27][CH2:28][C:29]2[O:30][C:1](=[O:2])[NH:32][N:31]=2)[CH:17]=[C:16]([C:13]([CH3:12])([CH3:14])[CH3:15])[C:21]=1[OH:22])([CH3:24])[CH3:25]

Participants

7

Reactant 4

HCID 1140TolueneHCID 6371PhosgeneHCID 648653,5-Di-tert-butyl-4-hydroxyhydrocinnamic acid hydrazideHCID 516892Sodium Bicarbonate

Product 1

HCID 9840004HCID 9840004, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 12.5% solution of phosgene in toluene (10.7 mL, 12.0 mmol) is added dropwise to a -78° C. solution of 3,5-bis(1,1-dimethylethyl)-4-hydroxybenzenepropanoic acid hydrazide in tetrahydrofuran (200 mL). The reaction mixture is stirred for 10 minutes then poured into a separatory funnel containing ethyl acetate and aqueous sodium bicarbonate. The organic phase is washed three times with water and once with brine. Drying the organic phase over magnesium sulfate and evaporation gives a crude product which is crystallized from hexane to afford 1.6 g (74%) of 5-[2-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]ethyl]-1,3,4-oxadiazol-2(3H)-one, mp 120.0°-123.0° C.

Workup

  1. additionthen poured into a separatory funnel
  2. washThe organic phase is washed three times with water
  3. customDrying the organic phase
  4. customover magnesium sulfate and evaporation
  5. customgives a crude product which
  6. customis crystallized from hexane

Sources & evidence

ORD record
ord-bce2b2cb90884a7d991974241c0ecf20
Source dataset
uspto-grants-1992_04
Patent number
US05102897

Reaction notes

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