Hydrochloric Acid → HCID 22709072, compound

HRID 352266Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.Cl[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:20].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:20])[CH:6]=[CH:5]2

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 6-bromo2-naphthol (22.30 g), 6-chloro-1-hexanol (20.50 g), potassium carbonate (20.50 g) and potassium iodide (1.50 g) in dimethylformamide (DMF, 100 ml) was heated at 100° C for 4 h. The mixture was then cooled and poured into 150 ml of HCl (3N) and extracted with ether (3×200 ml). The combined ether extracts were washed with saturated NaCl solution (200 ml), dried over magnesium sulfate, evaporated to give a brownish oil and filtered through a silica gel column (150 g,) using dichloromethane as eluent to give a brownish solid. The brown solid was recrystallised from hexane/dichloromethane (9/1) to give 24.8 g of 6-(6bromo-naphthalen-2-yloxy)hexan-1-ol as white needles.

Workup

temperatureThe mixture was then cooled
extractionextracted with ether (3×200 ml)
washThe combined ether extracts were washed with saturated NaCl solution (200 ml)
dry with materialdried over magnesium sulfate
customevaporated
customto give a brownish oil
filtrationfiltered through a silica gel column (150 g,)
customto give a brownish solid
customThe brown solid was recrystallised from hexane/dichloromethane (9/1)

Sources & evidence

ORD record: ord-89c0dc6640be4bd3a8bd4f50260e04fa
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06746729B1

Reaction notes

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