Benzoic Acid → HCID 178441401, compound

HRID 1493675Notes

Reaction equation

HRID 1493675 reaction equation
C(=O)([O-])[O-].[Ba+2].[C:6]([OH:14])(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:15][CH2:16][CH2:17][CH2:18][CH:19]1[C:54](=[O:55])[O:53][CH:52]([CH:56]([CH:58]([OH:66])[CH2:59][CH2:60][CH2:61][NH:62][C:63]([NH2:65])=[NH:64])[CH3:57])[CH:51]([CH3:67])[CH:50]=[C:49]([CH3:68])[CH2:48][CH2:47][CH2:46][CH2:45][CH:44]([OH:69])[CH2:43][CH:42]([OH:70])[CH2:41][CH:40]([OH:71])[CH2:39][CH:38]([OH:72])[CH2:37][CH:36]([OH:73])[CH:35]([O:74][C@H:75]2[O:79][C@H:78]([CH2:80][OH:81])[C@@H:77]([OH:82])[C@@H:76]2[OH:83])[CH:34]=[C:33]([CH3:84])[CH:32]([OH:85])[CH2:31][CH2:30][CH2:29][CH:28]([OH:86])[CH2:27][CH2:26][CH2:25][CH:24]([OH:87])[CH2:23][CH2:22][CH:21]([CH3:88])[CH:20]1[OH:89].S([O-])([O-])(=O)=O>CO>[CH3:15][CH2:16][CH2:17][CH2:18][CH:19]1[C:54](=[O:55])[O:53][CH:52]([CH:56]([CH:58]([OH:66])[CH2:59][CH2:60][CH2:61][NH:62][C:63]([NH2:65])=[NH:64])[CH3:57])[CH:51]([CH3:67])[CH:50]=[C:49]([CH3:68])[CH2:48][CH2:47][CH2:46][CH2:45][CH:44]([OH:69])[CH2:43][CH:42]([OH:70])[CH2:41][CH:40]([OH:71])[CH2:39][CH:38]([OH:72])[CH2:37][CH:36]([OH:73])[CH:35]([O:74][C@H:75]2[O:79][C@H:78]([CH2:80][OH:81])[C@@H:77]([OH:82])[C@@H:76]2[OH:83])[CH:34]=[C:33]([CH3:84])[CH:32]([OH:85])[CH2:31][CH2:30][CH2:29][CH:28]([OH:86])[CH2:27][CH2:26][CH2:25][CH:24]([OH:87])[CH2:23][CH2:22][CH:21]([CH3:88])[CH:20]1[OH:89].[C:6]([O-:14])(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 10563Barium CarbonateHCID 178441404HCID 178441404, compound

Product 1

HCID 178441401HCID 178441401, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

0.087 g (0.444 millimole) of barium carbonate are suspended in 15 ml of methanol whereupon 0.11 g (0.91 millimole) of benzoic acid is added. The suspension thus obtained is heated to boiling until a clear solution is obtained. The clear and colorless solution is added to a suspension of 1.0 g (0.887 millimoles) of primycin sulfate and 80 ml of methanol and the reaction mixture is heated to boiling for 20 minutes under stirring. The hot solution is filtered through Celite and the filtrate is evaporated to dryness in vacuo. The residue is treated with ether, filtered and the solid is washed on the filter with 15 ml of a 2:1 mixture of acetone and water. Thus 0.98 g of primycin benzoate is obtained in the form of a white powder, yield 90.6%. Mp.: 170°-171° C., /α/D25 =+36.9°.

Workup

  1. additionis added
  2. customThe suspension thus obtained
  3. temperatureis heated
  4. customis obtained
  5. temperaturethe reaction mixture is heated
  6. filtrationThe hot solution is filtered through Celite
  7. customthe filtrate is evaporated to dryness in vacuo
  8. additionThe residue is treated with ether
  9. filtrationfiltered
  10. washthe solid is washed on the
  11. filtrationfilter with 15 ml of a 2:1 mixture of acetone and water

Sources & evidence

ORD record
ord-7acba07a52094cf58b09aac16147d96e
Source dataset
uspto-grants-1991_06
Patent number
US05023242

Reaction notes

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