Thioglycolic Acid → HCID 20133523, compound

HRID 986309Notes

Reaction equation

HRID 986309 reaction equation
[SH:1][CH2:2][C:3]([OH:5])=[O:4].[Na].[CH2:7]([CH:9]1[O:11][CH2:10]1)Cl.[CH3:12][C:13]([C:16]1[CH:21]=[C:20]([SH:22])[CH:19]=[C:18]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:17]=1[OH:27])([CH3:15])[CH3:14]>C(O)C.O>[CH3:26][C:23]([C:18]1[CH:19]=[C:20]([S:22][CH2:7][CH:9]([OH:11])[CH2:10][S:1][CH2:2][C:3]([OH:5])=[O:4])[CH:21]=[C:16]([C:13]([CH3:15])([CH3:14])[CH3:12])[C:17]=1[OH:27])([CH3:24])[CH3:25]

Participants

7

Reactant 4

HCID 1133Thioglycolic AcidHCID 7835EpichlorohydrinHCID 703702,6-Di-tert-butyl-4-mercaptophenol2×HCID 5360545Sodium3×

Product 1

HCID 20133523HCID 20133523, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

Mercaptoacetic acid (1.32 g, 0.0144 mole) was added to a solution of ethyl alcohol (100 ml) containing sodium (0.66 g, 0.029 mole). The solution was stirred for 30 minutes and epichlorohydrin (1.33 g, 0.0144 mole) was added by syringe. A solution of the sodium salt of 2,6-bis(1,1-dimethylethyl)-4-mercaptophenol prepared from 2,6-bis(1,1-dimethylethyl)-4-mercaptophenol (3.43 g, 0.0144 mole) and sodium (0.33 g, 0.0144 mole) in ethyl alcohol (50 ml) was added dropwise and the reaction stirred for 72 hours at room temperature. Water (50 ml) was added and the ethyl alcohol removed using a rotary evaporator. The product was extracted into ethyl acetate, dried over sodium sulfate, filtered and concentrated. The product was isolated as an oil by chromatography on silica. The structure was confirmed by its NMR and IR spectra.

Workup

  1. additionwas added dropwise
  2. stirringthe reaction stirred for 72 hours at room temperature
  3. customthe ethyl alcohol removed
  4. customa rotary evaporator
  5. extractionThe product was extracted into ethyl acetate
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe product was isolated as an oil by chromatography on silica

Sources & evidence

ORD record
ord-e38f7b610b2b4a8ca0af2b7ccf393396
Source dataset
uspto-grants-1987_12
Patent number
US04711903

Reaction notes

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