1-Dodecanethiol → HCID 57707129, compound

HRID 1662505Notes

Reaction equation

HRID 1662505 reaction equation
[F:1][C:2]1[C:7]([O:8]C)=[CH:6][CH:5]=[CH:4][C:3]=1[CH:10]([CH2:15][CH3:16])[CH2:11][C:12]([OH:14])=[O:13].CN1C(=O)CCC1.[OH-].[Na+].C(S)CCCCCCCCCCC>Cl.CCOC(C)=O>[F:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:10]([CH2:15][CH3:16])[CH2:11][C:12]([OH:14])=[O:13]

Participants

7

Reactant 4

HCID 81951-DodecanethiolHCID 13387N-methyl-2-pyrrolidoneHCID 14798Sodium HydroxideHCID 577061663-(2-Fluoro-3-methoxyphenyl)pentanoic acid

Product 1

HCID 57707129HCID 57707129, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
125 °C

Procedure

A 500 mL round bottom flask was charged with 3-(2-fluoro-3-methoxyphenyl)pentanoic acid 77.D (3.44 g, 15.2 mmol), NMP (30 mL), NaOH (2.74 g, 68.4 mmol), and 1-dodecanethiol (available from Aldrich) (12.8 mL, 53.2 mmol). The mixture was stirred for 5 hours at 125° C. under N2, cooled to room temperature, and diluted with 1 N HCl and EtOAc. The combined organic layers were washed with water and brine, dried (MgSO4), and concentrated to afford 3-(2-fluoro-3-hydroxyphenyl)pentanoic acid 77.E as a yellow liquid (3.23 g). The product so obtained was used without further purification.

Workup

  1. temperaturecooled to room temperature
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fe6eb898db4a483c8f7a4450e78c5523
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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