Dimethyl Sulfoxide → 4-Isopropylcinnamaldehyde

HRID 12573

Reaction equation

HRID 12573 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH:11]([C:14]1[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[CH2:22][OH:23])=[CH:16][CH:15]=1)([CH3:13])[CH3:12].C(N(CC)CC)C>C(Cl)Cl>[CH:11]([C:14]1[CH:15]=[CH:16][C:17](/[CH:20]=[CH:21]/[CH:22]=[O:23])=[CH:18][CH:19]=1)([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 21961314(2E)-3-[4-(Propan-2-yl)phenyl]prop-2-en-1-ol2×

Product 1

HCID 53548974-Isopropylcinnamaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following General Procedure H, oxalyl chloride (9.5 ml, 19.0 mmol, 2M in CH2Cl2), DMSO (1.8 ml, 25.3 mmol), (E)-3-(4-isopropylphenyl)prop-2-en-1-ol (Compound 109, 2.2 g, 12.6 mmol) and triethylamine (7.1 ml, 50.7 mmol) in CH2Cl2 (100 ml) were reacted to obtain the title compound as an oil.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-91fe98f3a159420ea2965d62c2c78fad
Source dataset
uspto-grants-2010_06
Patent number
US07728014B2

Linked notes

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