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4-tert-Butylbenzoic acid → 4-tert-Butylbenzoic acid

HRID 1710307
Notes
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Reaction equation

HRID 1710307 reaction equation
[N+]([O-])([O-])=O.[Nd+3:5].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[C:14]([C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15].C(N(CC)CC)C>CO>[Nd:5].[C:14]([C:18]1[CH:19]=[CH:20][C:21]([C:22]([OH:24])=[O:23])=[CH:25][CH:26]=1)([CH3:17])([CH3:15])[CH3:16]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 74034-tert-Butylbenzoic acidHCID 8471TriethylamineHCID 10980413Neodymium(3+) hydrate trinitrate3×

Product 2

HCID 74034-tert-Butylbenzoic acidHCID 23934Neodymium

Reagents, catalysts & solvents 1

HCID 887Methanol
Solvent
4×

Conditions

Temperature
30 °C

Procedure

The compound was synthesized by the same method as that for Synthesis Example 1-2 above, that is, after forming a triethylamine salt of 4-tertiary-butylbenzoic acid in anhydrous methanol, a methanol solution of neodymium nitrate was added while stirring. Specifically, a reactor similar to that of 1-1 was used to stir a slurry solution obtained by adding 100 ml of an anhydrous methanol to 53.48 g (0.3 mol) of 4-tertiary-butylbenzoic acid, while dripping 30.4 g (0.3 mol) of triethylamine while maintaining at 30° C. by cooling in an ice water bath. After dripping, the solution was heated for 30 minutes at 40° C. to prepare a transparent synthesis solution of 4-tertiary-butylbenzoic acid-triethylamine salts. Next, 200 ml of methanol were further added to this synthesis solution and maintained at about 30° C., and a solution obtained by dissolving 43.8 g of neodymium nitrate into 100 ml of methanol was dripped in while stirring. Upon dripping of about half of the neodymium nitrate solution, it began to cloud, upon completion of dripping, a high-concentration slurry solution was obtained. After completion of dripping, the solution was heated to 40° C. for 30 minutes, to produce a slurry solution of a neodymium salt of 4-tertiary-butylbenzoic acid. Crystals obtained by filtering this slurry solution were added to 400 ml of methanol, stirred and washed, then refiltered, and 400 ml of methanol were once again added to the crystals stirred and washed, then filtered. The resulting crystals were dried under reduced pressure at 50° C., to obtain 59.3 g of a neodymium salt of 4-tertiary-butylbenzoic acid (yield 88%

Workup

  1. customSpecifically, a reactor similar to that of 1-1 was used
  2. stirringto stir a slurry solution
  3. customobtained
  4. temperatureby cooling in an ice water bath
  5. temperaturethe solution was heated for 30 minutes at 40° C.
  6. temperaturemaintained at about 30° C.
  7. customa solution obtained
  8. stirringwhile stirring
  9. customa high-concentration slurry solution was obtained
  10. temperaturethe solution was heated to 40° C. for 30 minutes

Sources & evidence

ORD record
ord-afca80da9ec54a128ce2ad36035b67f5
Source dataset
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07790290B2

Reaction notes

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