Dimethyl Sulfoxide → p-Methylcinnamaldehyde

HRID 12534

Reaction equation

HRID 12534 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][C:12]1[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[CH2:20][OH:21])=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:11][C:12]1[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[CH:20]=[O:21])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 53874824-Methylcinnamyl alcohol2×

Product 1

HCID 5371802p-Methylcinnamaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following General Procedure H, oxalyl chloride (7.1 ml, 14.2 mmol, 2 M in CH2Cl2), DMSO (1.3 ml, 18.9 mmol), (E)-3-(4-methylphenyl)prop-2-en-1-ol (Compound 41, 1.4 g, 9.5 mmol) and triethylamine (4.4 ml, 31.4 mmol) in CH2Cl2 (5 ml) were reacted to obtain the title compound as an oil.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-ff46d30221ab41f09c751f2de95c3f11
Source dataset
uspto-grants-2010_06
Patent number
US07728014B2

Linked notes

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