Isobutylene oxide → HCID 20133513, compound

HRID 359739Notes

Reaction equation

HRID 359739 reaction equation
[O-]CC.[Na+].[Na].[CH3:6][C:7]([C:10]1[CH:15]=[C:14]([SH:16])[CH:13]=[C:12]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:11]=1[OH:21])([CH3:9])[CH3:8].[CH3:22][C:23]1([CH3:26])[O:25][CH2:24]1>C(O)C>[CH3:18][C:17]([C:12]1[CH:13]=[C:14]([S:16][CH2:22][C:23]([OH:25])([CH3:26])[CH3:24])[CH:15]=[C:10]([C:7]([CH3:6])([CH3:8])[CH3:9])[C:11]=1[OH:21])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 11208Isobutylene oxideHCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 20133513HCID 20133513, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of sodium ethoxide, freshly prepared from sodium (1.31 g, 57.2 mmole) in ethyl alcohol (200 ml), was added 2,6-bis(1,1-dimethylethyl)-4-mercaptophenol (6.8 g, 28.6 mmole) and the mixture was stirred for one hour. After cooling to 5° C. with an ice bath, 1,1-dimethylethylene oxide (2.06 g, 28.6 mmole) was added and the ice bath removed. After stirring for 5.5 hours the reaction mixture was poured into 10% hydrochloric acid. The ethyl alcohol was removed in vacuo and the aqueous residue was extracted with ethyl acetate. The extracts were combined, dried over sodium sulfate, filtered, and concentrated to give 2,6-bis (1,1-dimethylethyl)-4-[(2-hydroxy-2-methylpropyl)thio]phenol. Trifluoroacetic acid (3 ml) was added to a solution of the phenol intermediate (2.2 g, 7 mmole), followed by addition by syringe of methyl thioglycolate (0.7 g, 6.7 mmole). After three hours the mixture was poured into water (100 ml) and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to an oil. Chromatography on silica gel gave the title dithio compound, m.p. 64°-68°.

Workup

  1. customthe ice bath removed
  2. stirringAfter stirring for 5.5 hours the reaction mixture
  3. additionwas poured into 10% hydrochloric acid
  4. customThe ethyl alcohol was removed in vacuo
  5. extractionthe aqueous residue was extracted with ethyl acetate
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4b39357762cb466a828cf83cad298811
Source dataset
uspto-grants-1991_03
Patent number
US05002967

Reaction notes

Loading…