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Hydrochloric Acid → 12-Hydroxy-8-(methanesulfonyl)heptadecanoic acid

HRID 262999
Notes
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Reaction equation

HRID 262999 reaction equation
COC([C:5]([S:29]([CH3:32])(=[O:31])=[O:30])([CH2:16][CH2:17][CH2:18][CH:19]([O:25]C(=O)C)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14]C)=[O:13])=O.[Cl-].[Na+].CS(C)=O.Cl>O>[CH3:32][S:29]([CH:5]([CH2:16][CH2:17][CH2:18][CH:19]([OH:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])(=[O:30])=[O:31]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 5234Sodium ChlorideHCID 21317603Methyl 8-methoxycarbonyl-8-methylsulfonyl-12-acetoxyheptadecanoate

Product 1

HCID 2021027912-Hydroxy-8-(methanesulfonyl)heptadecanoic acidYield 110.4%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent
2×

Conditions

Temperature
185 °C

Procedure

A mixture of methyl 8-methoxycarbonyl-8-methylsulfonyl-12-acetoxyheptadecanoate (36.7 g., 0.077 mole), sodium chloride (4.68 g., 0.08 mole), water (1 ml.) and dimethylsulfoxide (60 ml.) is heated in a bath maintained at 185° C. under nitrogen for 5 hours. The resulting reaction mixture is concentrated in vacuo at 100° C. providing an oily residue which is diluted with water. The aqueous mixture is acidified to Congo Red with 6N hydrochloric acid and extracted with ether. The organic extract is washed with water, dried over magnesium sulfate, filtered and evaporated in vacuo leaving the title compound as a viscous oil (31 g., 95%), pmr (CDCl3) δ 2.0 (s, 3H), 2.82 (s, 3H), 3.63 (s, 3H) and 4.9 (b, H).

Workup

  1. temperatureis heated in a bath
  2. customThe resulting reaction mixture
  3. concentrationis concentrated in vacuo at 100° C.
  4. customproviding an oily residue which
  5. extractionextracted with ether
  6. extractionThe organic extract
  7. washis washed with water
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-650ecb0a1bd54c7cbc26ce482de136f3
Source dataset
uspto-grants-1979_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04155908

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes