Hydrochloric Acid → (1R,cis)-2,2-dimethyl-3-(2-methyl-1,3-dioxolan-2-ylmethyl)-cyclopropanecarboxyic acid

HRID 28119Notes

Reaction equation

HRID 28119 reaction equation
[CH3:1][C:2]1([CH3:16])[C@@H:4]([CH2:5][C:6]2([CH3:11])[O:10][CH2:9][CH2:8][O:7]2)[C@H:3]1[C:12]([O:14]C)=[O:13].[OH-].[Na+].Cl>CO.O>[CH3:1][C:2]1([CH3:16])[C@@H:4]([CH2:5][C:6]2([CH3:11])[O:10][CH2:9][CH2:8][O:7]2)[C@H:3]1[C:12]([OH:14])=[O:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131711900HCID 131711900, compound

Product 1

HCID 54153659(1R,cis)-2,2-dimethyl-3-(2-methyl-1,3-dioxolan-2-ylmethyl)-cyclopropanecarboxyic acidYield 59.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
51 °C

Procedure

To a solution of 0.8 g of methyl (1R,cis)-2,2-dimethyl-3-(2-methyl-1,3-dioxolan-2-ylmethyl)cyclopropanecarboxylate in 5 ml of methanol, was added 1.6 ml of a 10% aqueous sodium hydroxide solution. The mixture was heated at 51° C. for 16 hours. The resulting mixture was diluted with water, acidified to pH 3 with 1 N hydrochloric acid, extracted with diethyl ether, and the extract was dried over magnesium sulfate and stripped to give 0.45 g of the desired product as a clear oil.

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialthe extract was dried over magnesium sulfate

Sources & evidence

ORD record
ord-e713b851bfee42ee89e533e6088c3d55
Source dataset
uspto-grants-1980_09
Patent number
US04225612

Reaction notes

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