Water → 4-(2,2-Dimethyl-1,3-dioxolan-4-yl)methoxyphenylethan-2-ol

HRID 652536Notes

Reaction equation

HRID 652536 reaction equation
CC1(C)OC(CS([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20]C)=O)=[CH:13][CH:12]=2)(=O)=O)CO1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH2:29].[OH-:30].[Na+]>O1CCCC1>[CH3:12][C:11]1([CH3:16])[O:30][CH:17]([CH2:18][O:20][C:11]2[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][OH:20])=[CH:15][CH:16]=2)[CH2:14][O:29]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 20197410Methyl 4-(2,2-dimethyl-1,3-dioxolan-4-yl)methylsulfonylphenylacetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 139239034-(2,2-Dimethyl-1,3-dioxolan-4-yl)methoxyphenylethan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 27 g. (0.096 mol) of methyl 4-(2,2-dimethyl-1,3-dioxolan-4-yl)methoxyphenylacetate (3) in 200 mL of tetrahydrofuran (THF) was added slowly to a stirred suspension of 4.0 g of LAH in 300 mL of THF. The mixture was stirred 2 h at room temperature and then treated sequentially with 4 mL of water, 4 mL of 15% NaOH solution, and 12 mL of water. The mixture was filtered and the filtrate evaporated to a residue which was triturated with hexane to afford 24 g of 4-(2,2-dimethyl-1,3-dioxolan-4-yl)methoxyphenylethan-2-ol (4) as a tan solid.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated to a residue which
  3. customwas triturated with hexane

Sources & evidence

ORD record
ord-d4afbde7fb574656804e312c83075748
Source dataset
uspto-grants-1987_06
Patent number
US04672071

Reaction notes

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