Lithium hydroxide, monohydrate → (Rs)-(e)-4-[3-(4,4-dimethyl-thiochroman-6-yl)-oct-1-enyl]-benzoic acid

HRID 394937Notes

Reaction equation

HRID 394937 reaction equation
[CH3:1][C:2]1([CH3:30])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])/[CH:13]=[CH:14]/[C:15]3[CH:24]=[CH:23][C:18]([C:19]([O:21]C)=[O:20])=[CH:17][CH:16]=3)[CH:10]=2)[S:5][CH2:4][CH2:3]1.O.[OH-].[Li+]>C1COCC1.O.CCOCC>[CH3:1][C:2]1([CH3:30])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])/[CH:13]=[CH:14]/[C:15]3[CH:16]=[CH:17][C:18]([C:19]([OH:21])=[O:20])=[CH:23][CH:24]=3)[CH:10]=2)[S:5][CH2:4][CH2:3]1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 18177895(Rs)-(e)-methyl 4-[3-(4,4-dimethyl-thiochroman-6-yl)-oct-1-enyl]-benzoate

Product 1

HCID 10223187(Rs)-(e)-4-[3-(4,4-dimethyl-thiochroman-6-yl)-oct-1-enyl]-benzoic acidYield 95.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

200 mg of (RS)-(E)-methyl 4-[3-(4,4-dimethyl-thiochroman-6-yl)-oct-1-enyl]-benzoate were dissolved in 10 ml THF/3 ml water/3 ml methanol and 200 mg of lithium hydroxide hydrate were added. The mixture was stirred at room temperature 4 hours. The mixture was diluted with 10 ml water and acidified to pH 2 with 1N hydrochloric. The resulting suspension was taken in 50 ml ether and the phases were separated. The aqueous phase was extracted with three portions of 25 ml ether. The combined extracts were dried over MgSO4. The solvent was removed in vacuo and the crude product was purified by flash chromatography (SiO2, 10% methanol/methylene chloride) followed by recrystalization from hexanes, yielding 185 mg of product as white solid. M.p. 146-146.5° C.

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted with three portions of 25 ml ether
  3. dry with materialThe combined extracts were dried over MgSO4
  4. customThe solvent was removed in vacuo
  5. customthe crude product was purified by flash chromatography (SiO2, 10% methanol/methylene chloride)
  6. customfollowed by recrystalization from hexanes

Sources & evidence

ORD record
ord-e17ea63ba6c24df39a5135b5dd46443e
Source dataset
uspto-grants-2003_08
Patent number
US06603012B2

Reaction notes

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