Methanol → Methyl 10,12-pentacosadiynoate

HRID 396102

Reaction equation

HRID 396102 reaction equation
[C:1]([OH:27])(=[O:26])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[C:11][C:12]#[C:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].[CH3:28]O>S(=O)(=O)(O)O.C(Cl)(Cl)Cl>[C:1]([O:27][CH3:28])(=[O:26])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[C:11][C:12]#[C:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 2

HCID 887MethanolHCID 53843310,12-Pentacosadiynoic acid

Product 1

HCID 145561Methyl 10,12-pentacosadiynoate

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 6212ChloroformSolvent

Procedure

10,12-pentacosadiynoic acid (10 gm, GFS Chemicals) was dissolved in a solution containing 10 ml methanol (HPLC grade) and 10 ml chloroform (HPLC grade). The solution was stirred at room temperature and 10 drops of neat sulfuric acid was added drop wise. The solution was warmed to 100° F. for 2 hour. The reaction mixture was purified using column chromatography. The product (MePDA) was dried using a rotovap and the material stored in a chloroform solution. The solid form of MePDA was very unstable to polymerization and therefore kept dissolved in organic solutions.

Workup

  1. temperatureThe solution was warmed to 100° F. for 2 hour
  2. customThe reaction mixture was purified
  3. dry with materialThe product (MePDA) was dried
  4. customThe solid form of MePDA was very unstable to polymerization
  5. dissolutionkept dissolved in organic solutions

Sources & evidence

ORD record
ord-b2453d96b47543b990fbad02313c1a9d
Source dataset
uspto-grants-2003_08
Patent number
US06607744B1

Linked notes

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