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

HRID 1655428Notes

Reaction equation

HRID 1655428 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 1N 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

Workup

  1. temperaturethe reaction mixture was refluxed for 36 hours
  2. extractionThe reaction mixture was extracted twice with 100 ml of diethyl ether

Sources & evidence

ORD record
ord-e34b80ae33ce4ca8b9a64573494e3568
Source dataset
uspto-grants-1993_10
Patent number
US05250567

Reaction notes

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