Hexane → HCID 19101839, compound

HRID 358923Notes

Reaction equation

HRID 358923 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][Br:8].[OH-].[Na+].[CH:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][C:12]=1[S:21][CH2:22][CH2:23][OH:24].CCCCCC>CCOCC.O>[Br:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][O:24][CH2:23][CH2:22][S:21][C:12]1[CH:13]=[CH:14][C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:11]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 3055202-naphthalen-2-ylsulfanylethanol

Product 1

HCID 19101839HCID 19101839, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1,6-dibromohexane (9 ml), 50% w/v sodium hydroxide (40 ml), 2-(2-naphthalenyl)thioethanol (4 g), TAB (0.8 g) and hexane (30 ml) was stirred vigorously at 20°, under nitrogen for 4 h. Water (100 ml) and ether (100 ml) were added and the mixture was further extracted with ether (100, 2×50 ml). The combined, dried ether extracts were evaporated in vacuo to give a yellow oil. Purification by FCC eluting with light petroleum (b.p. 60°-80°):ether (30:1→1:1) gave the title compound as a white crystalline solid (5.7 g), m.p. 38°-40° (softens 36°).

Workup

  1. extractionthe mixture was further extracted with ether (100, 2×50 ml)
  2. customdried ether extracts were evaporated in vacuo
  3. customto give a yellow oil
  4. customPurification by FCC
  5. washeluting with light petroleum (b.p. 60°-80°)

Sources & evidence

ORD record
ord-279d162da3014682b14cdd7e50c21ff3
Source dataset
uspto-grants-1991_03
Patent number
US04997986

Reaction notes

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