Hydrochloric Acid → HCID 135840347, compound

HRID 1288593Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl.[CH2:19](Br)[CH:20]=[CH2:21].[C:23](=[S:25])=[S:24]>C(COC)OC>[C:11]([C:7]1[CH:8]=[C:9]([CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[OH:15])[C:23]([S:25][CH2:19][CH:20]=[CH2:21])=[S:24])([CH3:14])([CH3:13])[CH3:12]

Participants

Conditions

Temperature: 25 °C

Procedure

A 0.1 mol sample of 2,6-di-t-butylphenol was added dropwise to a solution of 0.2 mol sodium hydride (57% in mineral oil) in 150 ml dimethoxyethane under an atmosphere of nitrogen at about 25° C. After the addition was completed, the reaction mixture was stirred for one hour at 25° C. A 0.1 mol sample of carbon disulfide was then added and the resulting reaction mixture stirred at about 25° C. for 10 minutes. Concentrated hydrochloric acid (0.1 mol) was added slowly, followed by 0.1 mol allyl bromide in 50 ml dimethoxyethane. The reaction mixture was then heated at reflux overnight (about 16 hours). The reaction mixture was poured into ice water and the crystalline product recovered by filtration. Recrystallization from ether/hexane gave the product, which melted at 93°-95° C. Elemental analysis of the product is tabulated in Table I.

Workup

additionAfter the addition
customthe resulting reaction mixture
stirringstirred at about 25° C. for 10 minutes
temperatureThe reaction mixture was then heated
temperatureat reflux overnight (about 16 hours)
filtrationthe crystalline product recovered by filtration
customRecrystallization from ether/hexane
customgave the product, which melted at 93°-95° C

Sources & evidence

ORD record: ord-2cc1b20bdd1845619fe99a978f242b03
Source dataset: uspto-grants-1976_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03988471

Reaction notes

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