3,5-Dimethyl-4-hydroxybenzonitrile → Benzonitrile, 3,5-dimethyl-4-(4-pentynyloxy)-

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:11])[C:9]=1[OH:10])[C:5]#[N:6].Cl[CH2:13][CH2:14][CH2:15][C:16]#[CH:17]>>[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:11])[C:9]=1[O:10][CH2:17][CH2:16][CH2:15][C:14]#[CH:13])[C:5]#[N:6]

Participants

Reactant 2

HCID 201763,5-Dimethyl-4-hydroxybenzonitrile

HCID 843081-Pentyne, 5-chloro-

Product 1

HCID 10059076Benzonitrile, 3,5-dimethyl-4-(4-pentynyloxy)-Yield 99.4%

Procedure

Following the procedure of Example 1c and using 14.7 g (100 mmol) of 3,5-dimethyl-4-hydroxybenzonitrile and substituting 5-chloro-1-pentyne (12.7 mL, 120 mmol) for the product of Example 1b, there was obtained a red-brown oil which was purified by chromatography (Silica Gel 60, 15% ethyl acetate in hexanes) to give pure title compound (21.2 g, 99.4%) as a pale yellow oil.

Workup

customthere was obtained a red-brown oil which
customwas purified by chromatography (Silica Gel 60, 15% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-9b1c9abd9bfb485cab308f098a71e8db
Source dataset: uspto-grants-1995_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05464848

Reaction notes

Loading…