Toluene → HCID 73996776, compound

HRID 1355421Notes

Reaction equation

HRID 1355421 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][CH:12]([CH2:15][CH2:16][CH2:17][CH3:18])[CH:13]=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:19]1(C)[CH:24]=CC=[CH:21][CH:20]=1.CC(O)C=C.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH2:15]([C:12]([CH2:11][S:8]([C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=1)(=[O:10])=[O:9])([CH2:24][CH:19]=[CH:20][CH3:21])[CH:13]=[O:14])[CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 117163-Buten-2-olHCID 14640309HCID 14640309, compound

Product 1

HCID 73996776HCID 73996776, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Advantageously, the conversion of 18a to 47 and the conversion of 47 to 31 can be carried out sequentially or simultaneously in a single reaction vessel or in a single reaction mixture without isolation. To further advantage, the preparation of the acetal 18 from aldehyde 19, the conversion of 18 to the corresponding enol ether intermediate, and the conversion of the enol ether intermediate to 31 can all be carried out in a single reaction vessel or reaction mixture. For example, 2-(((4-methylphenyl)sulfonyl)methyl)hexanal can be heated in a solvent such as toluene in the presence of 3-buten-2-ol and p-toluenesulfonic acid with removal of water (e.g., with a Dean-Stark trap) to produce 2-butyl-2-(((4-methylphenyl)sulfonyl)methyl)hex-4-enal.

Workup

  1. customreaction mixture

Sources & evidence

ORD record
ord-be4e607ebfb849c283759df21736bf53
Source dataset
uspto-grants-2003_07
Patent number
US06586434B2

Reaction notes

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