Hydrochloric Acid → HCID 58154779, compound

HRID 2359390Notes

Reaction equation

HRID 2359390 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].Cl[CH2:13][C@@H:14]1[CH2:18][O:17][C:16]([CH3:20])([CH3:19])[O:15]1.C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C.O>[CH3:19][C:16]1([CH3:20])[O:15][C@H:14]([CH2:13][O:1][C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH2:18][O:17]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 88068Methyl 3-HydroxybenzoateHCID 6930483(S)-4-Chloromethyl-2,2-dimethyl-1,3-dioxolane

Product 1

HCID 58154779HCID 58154779, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of methyl 3-hydroxybenzoate (10.0 g, 65.8 mmol), (S)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane (13.0 g, 98.7 mmol) and K2CO3 (18.0 g, 132 mmol) in DMF (100 ml) was stirred for 18 h at 160° C. The mixture was diluted with water (150 mL) and adjusted to pH=6 by the addition of 3N HCl. The mixture was extracted with ethyl acetate (200 ml×3) and the combined organic layers were dried (MgSO4) and concentrated under reduced pressure. The residue was purified by column chromatography (10% Ethyl acetate in petroleum ether) to give (R)-methyl 3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)benzoate as a brown oil, (8.5 g, 49% yield).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (200 ml×3)
  2. dry with materialthe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography (10% Ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-4a21e543481e4651babafd9b35d1fd4d
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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