Ethyl Acrylate → 2-Propenoic acid, 3-(2-naphthalenyl)-, ethyl ester

HRID 1156456Notes

Reaction equation

[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11](Cl)=O.[C:14]([O:18][CH2:19][CH3:20])(=[O:17])[CH:15]=C>>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=[CH:15][C:14]([O:18][CH2:19][CH3:20])=[O:17]

Participants

Reactant 2

HCID 8821Ethyl Acrylate

HCID 752462-Naphthoyl chloride

Product 1

HCID 44543982-Propenoic acid, 3-(2-naphthalenyl)-, ethyl esterYield 88%

Procedure

The procedure described in Example 28 is repeated, except that 9.55 g (0.05 mol) of 2-naphthoyl chloride and 6.25 g (0.0625 mol) of ethyl acrylate are used. After a reaction time of 2 hours at 120° C., 9.9 g (0.044 mol) of ethyl β-(2-naphthyl)-acrylate are obtained, corresponding to a yield of 88% of theory; boiling point 106°-110° C./4 Pa. Analysis for C15H14O2 (molecular weight 188): calculated C 79.62%, H 6.24%, O 14.14%; found C 79.39%, H 6.49%, O 14.08%.

Sources & evidence

ORD record: ord-d2cd1bb9c3554e799e8a018e4b9a19c5
Source dataset: uspto-grants-1982_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04335054

Reaction notes

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