1-Bromooctadecane → HCID 19389007, compound

HRID 1110316Notes

Reaction equation

HRID 1110316 reaction equation
COC(=S)C1C=C(C)C=C(O)C=1.BrCCCCCCCCCCCCCCCCCC.C(=O)([O-])[O-].[K+].[K+].C[O:39][C:40](=[O:68])[C:41]1[CH:46]=[C:45]([O:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH3:65])[CH:44]=[C:43]([S:66][CH3:67])[CH:42]=1.[OH-].[Na+]>CO>[CH3:67][S:66][C:43]1[CH:42]=[C:41]([CH:46]=[C:45]([O:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH3:65])[CH:44]=1)[C:40]([OH:68])=[O:39]

Participants

7

Reactant 5

HCID 82181-BromooctadecaneHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 53653037HCID 53653037, compoundHCID 54411747HCID 54411747, compound2×

Product 1

HCID 19389007HCID 19389007, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2.54 g (12.8 mmol) of 3-hydroxy-5-methylthiobenzoic acid methyl ester, 4.7 g (14.1 mmol) of 1-bromooctadecane and 2.7 g (19.2 mmol) of potassium carbonate in 60 ml of anhydrous DMP was stirred and heated at 80° under an argon atmosphere for 21 hours. The reaction mixture was filtered through a Celite pad and the filtrate was concentrated at reduced pressure. Water was added to the residue and the product was filtered and recrystallized from methylene chloride-methanol to give 5.5 g (95% yield), mp 64°-66°, of 3-(methylthio)-5-(octadecyloxy)benzoic acid methyl ester. The nmr and mass spectra were consistent with the structure. A solution of 2.7 g (6 mmol) of 3-(methylthio)-5-(octadecyloxy)benzoic acid methyl ester and 5.0 ml (30 mmol) of 6 N NaOH in 125 ml of methanol was stirred at reflux under argon for 5 hours. The solvent was removed at reduced pressure, the residue was acidified with 6 N HCl and the product was extracted with chloroform. The dried extract was concentrated to a solid which was triturated with hexane and filtered to give 2.6 g, mp 90°-92°, of 3-(methylthio)-5-(oxtadecyloxy)benzoic acid. The nmr and mass spectra were consistent with the structure.

Workup

  1. temperatureheated at 80° under an argon atmosphere for 21 hours
  2. filtrationThe reaction mixture was filtered through a Celite pad
  3. concentrationthe filtrate was concentrated at reduced pressure
  4. additionWater was added to the residue
  5. filtrationthe product was filtered
  6. customrecrystallized from methylene chloride-methanol
  7. customto give 5.5 g (95% yield), mp 64°-66°
  8. temperatureat reflux under argon for 5 hours
  9. customThe solvent was removed at reduced pressure
  10. extractionthe product was extracted with chloroform
  11. extractionThe dried extract
  12. concentrationwas concentrated to a solid which
  13. customwas triturated with hexane
  14. filtrationfiltered
  15. customto give 2.6 g, mp 90°-92°

Sources & evidence

ORD record
ord-c45171a33cc646749f8ecc3e568431da
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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