1-Naphthol → HCID 66632715, compound

HRID 1824729Notes

Reaction equation

HRID 1824729 reaction equation
[CH2:1]([O:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]=[O:18])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C(OCl)(C)(C)C.CCN(C(C)C)C(C)C.[C:34]1([OH:44])[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36][CH:35]=1>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[C:34]1([O:44][C:17]([C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:7]([O:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:8][CH:9]=2)=[O:18])[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36][CH:35]=1

Participants

7

Reactant 4

HCID 70051-NaphtholHCID 81531DiisopropylethylamineHCID 521297Tert-Butyl hypochloriteHCID 22144312HCID 22144312, compound

Product 1

HCID 66632715HCID 66632715, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 4-pentyloxy-naphthalene-1-carbaldehyde (121 mg,.0.5 mmol) in CCl4 (2 mL) is treated with t-BuOCl (8.82 M, 170 μL, 1.5 mmol) and stirred at 50° C. for 1 h. After addition of DIEA (0.3 mL, 1.7 mmol) and 1-naphthol (216 mg, 1.5 mmol) the mixture is refluxed for 2 h and distributed between 1M KHCO3 (5 mL) and DCM (2×5 mL). The combined organic phases are dried over Na2SO4 and concentrated. Flash chromatography (cyclohexane/acetone) yields 82 mg (43%) of colourless crystals.

Workup

  1. temperatureis refluxed for 2 h
  2. dry with materialThe combined organic phases are dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-01ce5b6503204aaabadcedfd2f632bb7
Source dataset
uspto-grants-2006_05
Patent number
US07045533B2

Reaction notes

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