Isobutyl chloroformate → 4'-Hydroxyacetophenone

HRID 597299

Reaction equation

HRID 597299 reaction equation
CCCCC[C@H](O)/C=C/[C@@H]1[C@@H:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]CC(O)=O)[C:12](=[O:13])[CH:11]=C1.C([O:29]C(Cl)=O)C(C)C>C(N(CC)CC)C>[OH:29][C:17]1[CH:16]=[CH:15][C:14]([C:12](=[O:13])[CH3:11])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 62365Isobutyl chloroformateHCID 5281912Pga1

Product 1

HCID 74694'-Hydroxyacetophenone

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Following the procedure of Example 1 but using 0.508 g. of PGA1, 0.254 ml. of triethylamine, 0.238 ml. of isobutylchloroformate, and 0.309 g. of p-hydroxyacetophenone, there is obtained a crude residue. This residue is subjected to silica gel chromatography, eluting with ethyl acetate-hexane (2:3), followed by ethyl acetate-hexane (7:3). The residue obtained by concentration of selected fractions, 0.500 g., an oil, is the title compound, having Rf 0.4 (TLC on silica gel in ethyl acetate-hexane (1:1)).

Sources & evidence

ORD record
ord-80bbbdb1085349ce9728247c8d96d99f
Source dataset
uspto-grants-1977_03
Patent number
US04013707

Linked notes

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