4-Hydroxybenzaldehyde → HCID 53667499, compound

Participants

Role	Name	HCID	Charge
Reactant	4-Hydroxybenzaldehyde	HCID 126	—
Reactant	Benzoyl chloride	HCID 7412	—
Reactant	Cyclopropyl methyl ketone	HCID 13004	—
Reactant	2,4-Dichlorobenzaldehyde	HCID 13404	—
Reactant	3,4-Dichlorobenzaldehyde	HCID 22710	—
Reactant	4-(Trifluoromethyl)benzaldehyde	HCID 67996	—
Reactant	4-Fluorobenzaldehyde	HCID 68023	—
Reactant	p-(Trifluoromethoxy)benzaldehyde	HCID 69573	—
Reactant	4-Bromobenzaldehyde	HCID 70741	—
Reactant	2-(4-Carboxyphenyl)vinyl 1-ethylcyclopropyl ketone	HCID 53946672	—
Reactant	HCID 57098678	HCID 57098678	—
Product	HCID 53667499	HCID 53667499	—

Reaction Steps

By following the procedure of Preparation A1 above, cyclopropyl methyl ketone can be caused to react with 3,4-dichlorobenzaldehyde, 2,4-dichlorobenzaldehyde, 4-bromobenzaldehyde, 4-fluorobenzaldehyde, 4-hydroxybenzaldehyde, 4-trifluoromethoxybenzaldehyde or 4-trifluoromethylbenzaldehyde to give, respectively, 2-(3,4-dichlorophenyl)vinyl cyclopropyl ketone [III; Ar is 3,4--Cl2C6H3, R is H], 2-(2,4-dichlorophenyl)vinyl cyclopropyl ketone [III; Ar is 2,4--Cl2C6H3, R is H], 2-(4-bromophenyl)vinyl cyclopropyl ketone [III; Ar is 4--BrC6H4, R is H], 2-(4-fluorophenyl)vinyl cyclopropyl ketone [III; Ar is 4--FC6H4, R is H], 2-(4-hydroxyphenyl)vinyl cyclopropyl ketone [III; Ar is 4--HOC6H4, R is H], 2-(4-trifluoromethoxyphenyl)vinyl cyclopropyl ketone [III; Ar is 4--F3COC6H4, R is H], or 2-(4-trifluoromethylphenyl)vinyl cyclopropyl ketone [III; Ar is 4--F3CC6H4, R is H]. 2-(4-Hydroxyphenyl)vinyl cyclopropyl ketone can be esterified with benzoyl chloride to give 2-(4-benzoyloxyphenyl)vinyl cyclopropyl ketone [III; Ar is 4--C6H5COOC6H4, R is H].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US04166074
Source dataset	uspto-grants-1979_08
ORD ID	ord-00b78d6219094a23a83642418d299e09
Source note	uspto-grants-1979_08