Sulfuric Acid → (1-Hydroxymethylcyclopropyl)acetic acid methyl ester

HRID 1171840Notes

Reaction equation

HRID 1171840 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:15]([O-])(O)=O.[Na+]>CO>[OH:1][CH2:2][C:3]1([CH2:6][C:7]([O:9][CH3:15])=[O:8])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 22404474[1-(Hydroxymethyl)cyclopropyl]acetic acid2×

Product 1

HCID 29941748(1-Hydroxymethylcyclopropyl)acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5 g 2-[1-(hydroxymethyl)cyclopropyl]acetic acid (compound (13)) was dissolved in 65 ml methanol and 80 mg sulfuric acid was added. The reaction mixture was stirred overnight at room temperature; reaction progress was monitored by GC. The pH of the reaction mixture was adjusted to 7 with saturated NaHCO3. The reaction mixture was evaporated to dryness. 75 ml of ethyl acetate and 10 ml brine were added. The water layer was washed with 20 ml ethyl acetate. The combined organic layers were dried (Na2SO4) and evaporated to dryness, resulting in a yellow oil.

Workup

  1. customreaction progress
  2. customThe reaction mixture was evaporated to dryness
  3. addition75 ml of ethyl acetate and 10 ml brine were added
  4. washThe water layer was washed with 20 ml ethyl acetate
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. customevaporated to dryness
  7. customresulting in a yellow oil

Sources & evidence

ORD record
ord-fcc334dad86b4f2b87b20902222c03ff
Source dataset
uspto-grants-2010_11
Patent number
US07829716B2

Reaction notes

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