p-Toluenesulfonic acid → 1-{4-[2-(3,4-Bis-hydroxymethyl-phenyl)ethyl]-2-thienyl}-1-propanone

HRID 49353Notes

Reaction equation

HRID 49353 reaction equation
[CH2:1]([C:3]1([C:8]2[S:9][CH:10]=[C:11]([CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[C:17]([CH2:23][OH:24])[CH:16]=3)[CH:12]=2)OCC[O:4]1)[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O.O>[OH:24][CH2:23][C:17]1[CH:16]=[C:15]([CH2:14][CH2:13][C:11]2[CH:12]=[C:8]([C:3](=[O:4])[CH2:1][CH3:2])[S:9][CH:10]=2)[CH:20]=[CH:19][C:18]=1[CH2:21][OH:22]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 20636295(4-{2-[2-(2-Ethyl-[1,3]dioxolan-2-yl)-4-thienyl]-ethyl}-2-hydroxymethylphenyl)methanol

Product 1

HCID 698245861-{4-[2-(3,4-Bis-hydroxymethyl-phenyl)ethyl]-2-thienyl}-1-propanone

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

In a manner similar to that of Example 6(g), by reaction of 5.3 g (15 mmol) of (4-{2-[2-(2-ethyl-[1,3]dioxolan-2-yl)-4-thienyl]ethyl}-2-hydroxymethyl-phenyl)methanol with a solution of para-toluenesulphonic acid in an acetone/water mixture, the desired product is obtained in the form of a white powder (m=4 g; Y=86%).

Sources & evidence

ORD record
ord-d0f9a8be503b490fab39d34c6b821c9c
Source dataset
uspto-grants-2004_03
Patent number
US06706725B1

Reaction notes

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