Chloroacetic Acid → trans-[[4-[[3,5-bis(1,1-Dimethylethyl)-4-hydroxyphenyl]thio]tetrahydro-3-furanyl]oxy]acetic acid

HRID 1741689Notes

Reaction equation

HRID 1741689 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([S:16][C@@H:17]2[CH2:21][O:20][CH2:19][C@H:18]2[OH:22])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].Cl[CH2:24][C:25]([OH:27])=[O:26].[K].Cl>C(O)(C)(C)C>[CH3:15][C:12]([C:9]1[CH:8]=[C:7]([S:16][C@@H:17]2[CH2:21][O:20][CH2:19][C@H:18]2[O:22][CH2:24][C:25]([OH:27])=[O:26])[CH:6]=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[C:10]=1[OH:11])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 5462222PotassiumHCID 15224688trans-4-[[3,5-bis (1,1-Dimethylethyl)-4-hydroxyphenyl]thio]tetrahydro-3-furanol

Product 1

HCID 15287676trans-[[4-[[3,5-bis(1,1-Dimethylethyl)-4-hydroxyphenyl]thio]tetrahydro-3-furanyl]oxy]acetic acid

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

The compound of Example 2 (3.6 g, 0.011 mole) and chloroacetic acid (2.04 g, 0.022 mole) were added to t-butyl alcohol (40 ml) to which had been added potassium (1.39 g, 0.033 mole) and the reaction mixture was refluxed for 36 hours. The reaction mixture was cooled to room temperature, and 1 N hydrochloric acid (50 ml) was added slowly. The reaction mixture was extracted twice with 100 ml of diethyl ether. The combined diethyl ether extracts were washed with saturated sodium bicarbonate (2×100 ml), 1 N hydrochloric acid (10 ml) and brine (20 ml) dried over anhydrous sodium sulfate, filtered and concentrated in a rotary evaporator to give the crude product as an oil. The product was purified by silica gel chromatography and recrystallized from ethyl acetate-hexane. The structure was supported by NMR and infrared spectroscopy and elemental analysis.

Workup

  1. temperaturethe reaction mixture was refluxed for 36 hours
  2. extractionThe reaction mixture was extracted twice with 100 ml of diethyl ether
  3. washThe combined diethyl ether extracts were washed with saturated sodium bicarbonate (2×100 ml), 1 N hydrochloric acid (10 ml) and brine (20 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in a rotary evaporator

Sources & evidence

ORD record
ord-0668797df41549b58ca9f002f8f2bf34
Source dataset
uspto-grants-1994_08
Patent number
US05334616

Reaction notes

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