(S)-4-((2,6-dimethoxyphenoxy)methyl)-2,2-dimethyl-1,3-dioxolane → (R)-3-(2,6-Dimethoxyphenoxy)propane-1,2-diol

HRID 2407326Notes

Reaction equation

HRID 2407326 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[C:4]=1[O:5][CH2:6][C@H:7]1[CH2:11][O:10]C(C)(C)[O:8]1>CO>[CH3:19][O:18][C:14]1[CH:15]=[CH:16][CH:17]=[C:3]([O:2][CH3:1])[C:4]=1[O:5][CH2:6][C@H:7]([OH:8])[CH2:11][OH:10]

Participants

3

Reactant 1

HCID 10849486(S)-4-((2,6-dimethoxyphenoxy)methyl)-2,2-dimethyl-1,3-dioxolane

Product 1

HCID 10799347(R)-3-(2,6-Dimethoxyphenoxy)propane-1,2-diolYield 91.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (S)-4-((2,6-dimethoxyphenoxy)methyl)-2,2-dimethyl-1,3-dioxolane (2.91 g, 10.85 mmol) and Amberlyst 15® (1.60 g) in methanol (30 ml) were stirred for 5 d. The mixture was filtered and evaporated to dryness to give 2.26 g of the title compound.

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-786bff5d4b6d485c812ed495a6ecb242
Source dataset
uspto-grants-2014_08
Patent number
US08809536B2

Reaction notes

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