Toluene → HCID 10064622, compound

HRID 1029544Notes

Reaction equation

HRID 1029544 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]([CH:25]=[C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])[C:27]=1[OH:28])[O:19][CH2:20][C:21]([NH:23][NH2:24])=[O:22])([CH3:15])[CH3:14]>O1CCCC1.C(OCC)(=O)C>[CH3:15][C:13]([C:16]1[CH:17]=[C:18]([CH:25]=[C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])[C:27]=1[OH:28])[O:19][CH2:20][C:21]1[O:22][C:1](=[O:2])[NH:24][N:23]=1)([CH3:12])[CH3:14]

Participants

6

Reactant 3

HCID 1140TolueneHCID 6371PhosgeneHCID 10424537HCID 10424537, compound

Product 1

HCID 10064622HCID 10064622, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 12.5% solution of phosgene in toluene (2.4 mL, 2.7 mmol) is added dropwise to a -78° C. of [3,5-bis(1,1-dimethylethyl)-4-hydroxyphenoxy]-acetic acid hydrazide (0.40 g, 1.36 mmol) in tetrahydrofuran (25 mL). The reaction mixture is stirred for 30 minutes, diluted with ethyl acetate, and washed three times with water and once with brine. Drying the organic phase over magnesium sulfate and evaporation gives a pale yellow oil which is crystallized from ethyl acetate/hexane yielding 0.34 g (79%) of 5-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenoxy]methyl-1,3,4-oxadiazol-2(3H)-one; mp 138.0°-140.0° C.

Workup

  1. washwashed three times with water
  2. customDrying the organic phase
  3. customover magnesium sulfate and evaporation
  4. customgives a pale yellow oil which
  5. customis crystallized from ethyl acetate/hexane yielding 0.34 g (79%) of 5-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenoxy]methyl-1,3,4-oxadiazol-2(3H)-one

Sources & evidence

ORD record
ord-69a8454c079b4dd4bf484a5f631b85ba
Source dataset
uspto-grants-1992_04
Patent number
US05102897

Reaction notes

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