Diisobutylamine → 2-chloro-4-cyclopentylPhenol

HRID 991583

Reaction equation

HRID 991583 reaction equation
[CH:1]1([C:6]2[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(NCC(C)C)C(C)C.S(Cl)([Cl:25])(=O)=O>C1(C)C=CC=CC=1>[Cl:25][C:10]1[CH:11]=[C:6]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[CH:7]=[CH:8][C:9]=1[OH:12]

Participants

5

Reactant 3

HCID 8085DiisobutylamineHCID 152024-CyclopentylphenolHCID 24648Sulfuryl chloride

Product 1

HCID 122361442-chloro-4-cyclopentylPhenol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-cyclopentylphenol (4 g) and diisobutylamine (0.35 mL) in toluene (75 mL) was heated to 70° C. with stirring. Sulfuryl chloride (2.0 mL) was introduced via syringe and the reaction stirred for 2 h at 70° C., then cooled to room temperature. The reaction mixture was concentrated in vacuo and the resulting oil subjected to chromatography on silica gel using hexane/ethyl acetate eluent to afford the title compound (3.5 g). 1H NMR (400 MHz, CDCl3): δ7.19 (d, 1H, J=2.0 Hz); 7.06 (dd, 1H, J=2.2 Hz, 6.2 Hz); 6.94 (d, 1H, J=8.6 Hz); 5.37 (s, 1H); 2.92 (quint, 1H, J=7.0 Hz); 2.03 (m, 2H); 1.80 (m, 2H); 1.67 (m, 2H); 1.53 (m, 2H). MS: m/e=197(M+)

Workup

  1. stirringthe reaction stirred for 2 h at 70° C.
  2. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-b13a55d1bb844e5d950f9854b45f5d9e
Source dataset
uspto-grants-2002_10
Patent number
US06465497B2

Linked notes

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