M-Cresol → (But-3-yn-1-yloxy)benzene

Reaction equation

[C:1]1(S(OCC#C)(=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14]1([OH:20])C=C[CH:17]=[CH:16][CH:15]=1.C1C(O)=CC=CC=1C>>[CH2:14]([O:20][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:15][C:16]#[CH:17]

Participants

Reactant 3

HCID 342M-Cresol

HCID 996Phenol

HCID 802732-Propyn-1-ol, 1-benzenesulfonate

Product 1

HCID 9989389(But-3-yn-1-yloxy)benzene

Procedure

The procedure for Example 614 was used, substituting 3-butynyl p-toluenesulfonate for propargyl benzenesulfonate and phenol for m-cresol to provide Example 633. 1H NMR (500 MHz, CDCl3) δ 2.02 (t, J=2 Hz, 1H), 2.68 (dt, J=8, 2 Hz, 2H), 4.08 (t, J=8 Hz, 2H), 6.96 (m, 3H), 7.30 (m, 2H).

Workup

customto provide Example 633

Sources & evidence

ORD record: ord-b8104ef4b95b4bb2af8c738a67af23e9
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07468371B2

Reaction notes

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