Ethanol → HCID 59554587, compound

HRID 1171843Notes

Reaction equation

HRID 1171843 reaction equation
[OH:1][CH2:2][C:3]1([CH2:6][C:7]([OH:9])=[O:8])[CH2:5][CH2:4]1.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+].[CH2:20](O)[CH3:21]>>[OH:1][CH2:2][C:3]1([CH2:6][C:7]([O:9][CH2:20][CH3:21])=[O:8])[CH2:5][CH2:4]1

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 22404474[1-(Hydroxymethyl)cyclopropyl]acetic acid

Product 1

HCID 59554587HCID 59554587, compound

Procedure

7.1 g of crude (13) product was dissolved in 150 ml of ethanol. 1 ml of concentrated sulfuric acid was added and the solution was stirred at reflux for 2 hours. 50 ml of saturated aqueous sodium bicarbonate was added to the cooled mixture and the mixture was extracted twice with 100 ml of dichloromethane. The combined organic extracts were dried over anhydrous sodium sulfate and evaporated. The crude product was distilled at 100° C. at a reduced pressure affording a slightly yellow liquid (3.2 g).

Workup

  1. temperatureat reflux for 2 hours
  2. extractionthe mixture was extracted twice with 100 ml of dichloromethane
  3. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  4. customevaporated
  5. distillationThe crude product was distilled at 100° C. at a reduced pressure

Sources & evidence

ORD record
ord-7747086fd1bd4e7694fb58cb8cb77976
Source dataset
uspto-grants-2010_11
Patent number
US07829716B2

Reaction notes

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