(+)-3-[2-(Benzyloxy)-4-methoxyphenyl]-2-hydroxypropyl 4-methylbenzenesulfonate → (+/-)-2-Hydroxy-3-(2-hydroxy-4-methoxyphenyl)propyl 4-methylbenzenesulfonate

HRID 2115904Notes

Reaction equation

HRID 2115904 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH:13]([OH:31])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=2[O:23]CC2C=CC=CC=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1>C(O)C.[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][CH2:12][CH:13]([OH:31])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=2[OH:23])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 86599058(+)-3-[2-(Benzyloxy)-4-methoxyphenyl]-2-hydroxypropyl 4-methylbenzenesulfonate

Product 1

HCID 86599059(+/-)-2-Hydroxy-3-(2-hydroxy-4-methoxyphenyl)propyl 4-methylbenzenesulfonateYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (±)-3-[2-(benzyloxy)-4-methoxyphenyl]-2-hydroxypropyl 4-methylbenzenesulfonate (42.84 g, 0.097 mol) in ethanol (600 mL) was added palladium on carbon (10 wt. %, 5.81 g) and the reaction mixture was shaken under an H2 atmosphere (50 psi) for 6 h. The reaction mixture was filtered (celite) and the solvent removed in vacuo to provide 32.27 g (95%) of (±)-2-hydroxy-3-(2-hydroxy-4-methoxyphenyl)propyl 4-methylbenzenesulfonate as a colorless oil. Rf=0.34 (silica, ethyl acetate:hexanes 2:8); Anal. calcd. for C17H18O5S: C, 61.06; H, 5.43. Found: C, 60.70; H, 5.37.

Workup

  1. filtrationThe reaction mixture was filtered (celite)
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-ee51cb6ffe7d49cb99bd0a42a13e64ad
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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