Hydrochloric Acid → 4-(9-Methoxycarbonyl nonylsulfanyl) benzoic acid

HRID 445005Notes

Reaction equation

HRID 445005 reaction equation
[SH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31].Cl.[Na+].[Cl-]>C1COCC1.CO.CCOC(C)=O>[CH3:33][O:32][C:30]([CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][S:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)=[O:31]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 81531DiisopropylethylamineHCID 957384-Mercaptobenzoic acidHCID 554079Methyl 10-bromodecanoate

Product 1

HCID 667246304-(9-Methoxycarbonyl nonylsulfanyl) benzoic acidYield 100%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

4-Mercaptobenzoic acid (2.0 g, 13 mmol) was placed in THF (25 ml). DIEA (3.7 g, 28.5 mmol) was added followed by a solution of methyl 10-bromodecanoate (3.44 g, 13 mmol) in THF (10 ml). After 1 h the solvent was removed under vacuum to yield a slurry, which was stored at rt for 3 days. AcOEt (100 ml) and 1 N HCl (50 ml) were added, but the precipitate did not dissolve very well. Sat. NaCl was added and then methanol in order to aid phase separation. The aqueous phase was removed, and DCM was added to the organic phase, but the precipitates still did not dissolve. The organic phase was concentrated under vacuum and dried with toluene by adding and evaporating twice. Drying under vacuum yielded a white solid (4.4 g, quantitative yield).

Workup

  1. customAfter 1 h the solvent was removed under vacuum
  2. customto yield a slurry, which
  3. dissolutionthe precipitate did not dissolve very well
  4. customphase separation
  5. customThe aqueous phase was removed
  6. additionDCM was added to the organic phase
  7. customthe precipitates still
  8. dissolutiondid not dissolve
  9. concentrationThe organic phase was concentrated under vacuum
  10. dry with materialdried with toluene
  11. additionby adding
  12. customevaporating twice
  13. customDrying under vacuum

Sources & evidence

ORD record
ord-faec2b1b3e824bea88a82848e212668e
Source dataset
uspto-grants-2013_07
Patent number
US08476228B2

Reaction notes

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