4-Toluenesulfonyl chloride → HCID 86599063, compound

HRID 2115913Notes

Reaction equation

HRID 2115913 reaction equation
[CH2:1]([C:8]1[C:9]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:10]([CH2:14][CH:15]([OH:18])[CH2:16][OH:17])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>N1C=CC=CC=1>[CH3:37][C:27]1[CH:32]=[CH:31][C:30]([S:33]([O:17][CH2:16][CH:15]([OH:18])[CH2:14][C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:9]=2[O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:35])=[O:34])=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 68961793HCID 68961793, compound

Product 1

HCID 86599063HCID 86599063, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Treatment of (±)-3-[3-benzyl-2-(benzyloxy)phenyl]propane-1,2-diol (9.76 g, 0.028 mol) with p-toluenesulfonyl chloride (5.87 g, 0.031 mol) in pyridine (250 mL) generally according to the procedure described for Intermediate 3 gave 9.88 g (70%) of (±)-3-[3-benzyl-2-(benzyloxy)phenyl]-2-hydroxypropyl 4-methylbenzenesulfonate as a colorless oil. Anal. calcd. for C30H30O5S: C, 71.69; H, 6.02. Found: C, 70.41; H, 6.14.

Sources & evidence

ORD record
ord-7acb8b5c497c422f99aab931a44d0004
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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