Acetaldehyde → HCID 86639358, compound

HRID 1624188Notes

Reaction equation

HRID 1624188 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[CH:10](=O)[CH3:11].[Cl:13]CCl>[Cl-].[Zn+2].[Cl-]>[C:4]([O:6][CH2:11][CH2:10][Cl:13])(=[O:5])/[CH:3]=[CH:2]/[C:1]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 6344DichloromethaneHCID 5369209Monomethyl Fumarate

Product 1

HCID 86639358HCID 86639358, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

Adopting methods and procedures according to Iyer, et al., Synth. Commun. 1995, 25(18), 2739, chloroethyl methyl (2E)but-2-ene-1,4-dioate was prepared from methyl hydrogen fumarate (MHF), acetaldehyde, and anhydrous zinc(II) chloride in anhydrous dichloromethane (DCM). 1H NMR (CDCl3, 400 MHz): δ 6.95 (d, J=16.0 Hz, 1H), 6.85 (d, J=16.0 Hz, 1H), 6.60 (q, J=5.2 Hz, 1H), 3.81 (s, 3H), 1.83 (d, J=5.2 Hz, 3H).

Sources & evidence

ORD record
ord-fb4fc299e27c4250bff6d5be676d0e6c
Source dataset
uspto-grants-2014_07
Patent number
US08778991B2

Reaction notes

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