P-Cresol → Benzene, 1-(1,1-dimethylethyl)-4-(2-propynyloxy)-

Reaction equation

[CH:1]1[C:6](O)=CC=C(C)[CH:2]=1.[C:9]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10]>>[CH2:6]([O:19][C:16]1[CH:15]=[CH:14][C:13]([C:9]([CH3:12])([CH3:10])[CH3:11])=[CH:18][CH:17]=1)[C:1]#[CH:2]

Participants

Reactant 2

HCID 2879P-Cresol

HCID 73934-tert-Butylphenol

Product 1

HCID 142674Benzene, 1-(1,1-dimethylethyl)-4-(2-propynyloxy)-Yield 98%

Procedure

Example 14 is repeated except that p-cresol is replaced by 4-t-butylphenol. The product, 4-t-butylphenyl propargyl ether, is isolated as a colorless liquid in 98% yield and characterized by pmr spectroscopy. The product is represented by the following formula: ##STR24##

Sources & evidence

ORD record: ord-bdd2ec43859a47e4afb1a2bc73a38d15
Source dataset: uspto-grants-1989_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04885403

Reaction notes

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