HCID 13191786, compound → HCID 13191789, compound

HRID 1285012Notes

Reaction equation

HRID 1285012 reaction equation
[C:1]1([CH3:22])[CH:6]=[CH:5][C:4]([C:7]([C:9]2[CH:10]=[C:11]([CH:19]=[CH:20][CH:21]=2)[CH:12]=[CH:13][C:14]([O:16]CC)=[O:15])=O)=[CH:3][CH:2]=1.[N:23]1([CH2:28]/[CH:29]=[C:30](/[C:39]2[CH:40]=[C:41]([CH:47]=[CH:48][CH:49]=2)/[CH:42]=[CH:43]/[C:44]([OH:46])=[O:45])\[C:31]2[CH:36]=[CH:35][C:34](OC)=[CH:33][CH:32]=2)[CH2:27]C[CH2:25][CH2:24]1.N1(CC=C(C2C=C(C=CC=2)C=CC(OCC)=O)C2C=CC(OC)=CC=2)CCC[CH2:51]1>>[CH3:27][N:23]([CH3:28])[CH2:24]/[CH:25]=[C:7](/[C:9]1[CH:10]=[C:11]([CH:19]=[CH:20][CH:21]=1)/[CH:12]=[CH:13]/[C:14]([OH:16])=[O:15])\[C:4]1[CH:3]=[CH:2][C:1]([CH3:22])=[CH:6][CH:5]=1.[CH3:24][N:23]([CH3:27])[CH2:28]/[CH:29]=[C:30](\[C:39]1[CH:40]=[C:41]([CH:47]=[CH:48][CH:49]=1)/[CH:42]=[CH:43]/[C:44]([OH:46])=[O:45])/[C:31]1[CH:36]=[CH:35][C:34]([CH3:51])=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 13191786HCID 13191786, compoundHCID 54333784HCID 54333784, compoundHCID 54412100Ethyl 3-[3-(4-methylbenzoyl)phenyl]prop-2-enoate

Product 2

HCID 13191789HCID 13191789, compoundHCID 13191790HCID 13191790, compound

Procedure

By use of the methods described in Example 3,3-bromo-4'-methyl benzophenone (Ipatieff and Friedman, J. Amer. Chem. Soc., 1939, 61, 684) was converted into ethyl 3-(4-toluoyl)cinnamate, m.p. 86°-87°, and thence into a mixture of the (E)- and (Z)-isomers of ethyl 3-(3-dimethylamino-1-(4-tolyl)prop-1-enyl)cinnamate. Hydrolysis of this ester mixture and separation of the mixture of carboxylic acids by crystallization yielded (E)-3-(3-dimethylamino-1-(4-tolyl)prop-1E-enyl)cinnamic acid, m.p. 200°-205° C., and (E)-3-(3-dimethylamino-1-(4-tolyl)prop-1Z-enyl)cinnamic acid, m.p. 200°-205° C.

Workup

  1. customby crystallization

Sources & evidence

ORD record
ord-10d6ef6d22d94f5ea330902373459b80
Source dataset
uspto-grants-1986_01
Patent number
US04564685

Reaction notes

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