Acetic Acid → HCID 86597501, compound

HRID 2376796Notes

Reaction equation

HRID 2376796 reaction equation
COC(=O)[CH:4]([CH:11]1[CH2:13][CH:12]1[CH2:14][CH:15]1[O:19]CCO1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:21]([OH:24])(=[O:23])C.O.[C:26](=O)([O-])O.[Na+]>C(OCC)C>[CH3:26][O:24][C:21](=[O:23])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:11]1[CH2:13][CH:12]1[CH2:14][CH:15]=[O:19]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 86597502HCID 86597502, compound

Product 1

HCID 86597501HCID 86597501, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 8-((2-((1,3-dioxolan-2-yl)methyl)cyclopropyl)octanoic acid methyl ester (0.42 g), acetic acid (16 ml) and water (4 ml) was stirred at 60° C. overnight. The reaction mixture was poured into a mixture of ice, diethyl ether and a saturated aqueous solution of sodium hydrogencarbonate. The separated organic layer was washed with water and dried over magnesium sulfate. After filtration, the filtrate was concentrated in vacuo and the obtained residue was purified by chromatography on silica gel (eluted with 5% ethyl acetate in n-hexane). The fractions including 8-(2-(formylmethyl)cyclopropyl)octanoic acid methyl ester were collected and concentrated in vacuo to give 8-(2-(formylmethyl)cyclopropyl)octanoic acid methyl ester (0.11 g) as an oil.

Workup

  1. washThe separated organic layer was washed with water
  2. dry with materialdried over magnesium sulfate
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. customthe obtained residue was purified by chromatography on silica gel (eluted with 5% ethyl acetate in n-hexane)
  6. customwere collected
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cf726c8a2f634ace93627b7e1601c2f0
Source dataset
uspto-grants-2008_12
Patent number
US07468389B2

Reaction notes

Loading…