Hydrochloric Acid → HCID 18470383, compound

HRID 2228898Notes

Reaction equation

HRID 2228898 reaction equation
[H-].[Na+].[Br:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10].[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Br)=[CH:14][CH:13]=1.Cl>O1CCCC1>[Br:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][CH2:16][C:15]1[CH:18]=[CH:19][C:12]([Cl:11])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 779706-Bromo-1-hexanol

Product 1

HCID 18470383HCID 18470383, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

Sodium hydride (60%, 0.39 g) was added to a mixture of 6-bromohexanol (1.78 g) and 4-chlorobenzyl bromide (2.02 g) in dry tetrahydrofuran (150 ml). The mixture was stirred at 25° C. for 5 h and poured into 1M hydrochloric acid. Extraction with diethyl ether (3×), and washing the combined extracts with water and brine gave a solution that was dried over magnesium sulfate and evaporated under reduced pressure. The residue so obtained was chromatographed on silica gel using 40-60° C. petroleum ether to 10% diethyl ether in 40-60° C. petroleum ether as eluents. This gave 1-bromo-6-(4-chlorobenzyloxy)hexane (1.7 g). 1H-NMR (CDCl3) δ 1.3-1.55 (4H, m), 1.55-1.7 (2H, m), 1.75-1.95 (2H, m), 3.35-3.55 (4H, m), 4.46 (2H, s) and 7.2-7.4 (4H, m).

Workup

  1. extractionExtraction with diethyl ether (3×)
  2. washwashing the combined extracts with water and brine
  3. customgave a solution that
  4. dry with materialwas dried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue so obtained
  7. customwas chromatographed on silica gel using 40-60° C. petroleum ether to 10% diethyl ether in 40-60° C. petroleum ether as eluents

Sources & evidence

ORD record
ord-9225b007632b484db2b4a2429397929e
Source dataset
uspto-grants-2002_07
Patent number
US06417192B1

Reaction notes

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