1,6-Dibromohexane → HCID 15017845, compound

HRID 2248397Notes

Reaction equation

HRID 2248397 reaction equation
[O:1]1[C:5]([CH2:6][CH2:7][CH2:8][CH2:9][OH:10])=[CH:4][C:3]2[CH:11]=[CH:12][CH:13]=[CH:14][C:2]1=2.[Br:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]Br.[OH-].[Na+]>O>[Br:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]1[O:1][C:2]2[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=2[CH:4]=1

Participants

5

Reactant 3

HCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 17943330HCID 17943330, compound

Product 1

HCID 15017845HCID 15017845, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-benzo[b]furanbutanol (2 g), 1,6-dibromohexane (7.7 ml), TAB (500 mg) in 50% w/v sodium hydroxide solution (100 ml) was stirred at room temperature overnight. Water (100 ml) was added and the mixture extracted with ethyl acetate (2×100 ml). The combined organic extracts were dried and concentrated to give an oil. Purification by FCC eluting with hexane:ethyl acetate, 100:0→95:5) gave the title compound as a clear oil (2.1 g), t.l.c. (ether) Rf 0.83.

Workup

  1. extractionthe mixture extracted with ethyl acetate (2×100 ml)
  2. customThe combined organic extracts were dried
  3. concentrationconcentrated
  4. customto give an oil
  5. customPurification by FCC
  6. washeluting with hexane

Sources & evidence

ORD record
ord-4f76e64715b548c3910e19c89b5c626d
Source dataset
uspto-grants-1991_08
Patent number
US05039697

Reaction notes

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