Methanol → HCID 588910, compound

HRID 1720944Notes

Reaction equation

HRID 1720944 reaction equation
[O:1]=[C:2]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:14][CH2:15][C:16]([OH:18])=[O:17].S(=O)(=O)(O)O.[CH3:24]O>CCOCC>[O:1]=[C:2]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:14][CH2:15][C:16]([O:18][CH3:24])=[O:17]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 27750833-(2-oxocyclododecyl)propanoic acid

Product 1

HCID 588910HCID 588910, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 3-(2-oxocyclododecyl)-propionic acid (7.0 g, 27.5 mmol) in methanol (80 mL) was treated with concentrated sulfuric acid (0.3 mL, 5.4 mmol) and the mixture heated under reflux for 1 hour. After concentration of the reaction mixture in vacuo the residue was diluted with ether (1.1L) and washed sequentially with saturated sodium bicarbonate (100 mL) and water (2×100 mL). The organic phase was dried over magnesium sulfate and evaporated in vacuo to a crude oil (7.1 g, 96%). Purification by flash column chromatography on silica gel (100:1 ratio) by elution with hexane/ethyl acetate (95/5) afforded 6.1 g (83% yield) of the title compound as a waxy solid on cooling, m.p. 33°-35° C.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 1 hour
  3. washwashed sequentially with saturated sodium bicarbonate (100 mL) and water (2×100 mL)
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. customevaporated in vacuo to a crude oil (7.1 g, 96%)
  6. customPurification by flash column chromatography on silica gel (100:1 ratio)
  7. washby elution with hexane/ethyl acetate (95/5)

Sources & evidence

ORD record
ord-99cab84570394fa7822e91724565192a
Source dataset
uspto-grants-1996_04
Patent number
US05508302

Reaction notes

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