Ethanol → HCID 59554587, compound

HRID 1171845Notes

Reaction equation

HRID 1171845 reaction equation
[OH:1][CH2:2][C:3]1([CH2:6][C:7]([OH:9])=[O:8])[CH2:5][CH2:4]1.[CH2:10](O)[CH3:11]>S(=O)(=O)(O)O>[OH:1][CH2:2][C:3]1([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 702EthanolHCID 22404474[1-(Hydroxymethyl)cyclopropyl]acetic acid2×

Product 1

HCID 59554587HCID 59554587, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

6.0 g 2-[1-(hydroxymethyl)cyclopropyl]acetic acid (compound (13) was dissolved in 120 ml ethanol followed by addition of 6 drops of conc. sulfuric acid. The mixture was stirred at room temperature overnight. The mixture was concentrated partly to remove ˜40 ml ethanol and further stirred at room temperature (“rt”) for another day. The mixture was neutralized to pH˜7 (using ˜3 ml aq. saturated NaHCO3) and concentrated in vacuo. After re-dissolving in ethylacetate (200 ml), it was washed with brine (15 ml), dried and concentrated in vacuo to give a light-yellow oil (6.85 g).

Workup

  1. concentrationThe mixture was concentrated partly
  2. customto remove ˜40 ml ethanol
  3. stirringfurther stirred at room temperature (“rt”) for another day
  4. concentrationconcentrated in vacuo
  5. dissolutionAfter re-dissolving in ethylacetate (200 ml)
  6. washit was washed with brine (15 ml)
  7. customdried
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4ef946653fe24551938b48d30da69abf
Source dataset
uspto-grants-2010_11
Patent number
US07829716B2

Reaction notes

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