Sulfuric Acid → dihexadecyl propanedioate

HRID 2088325Notes

Reaction equation

HRID 2088325 reaction equation
OS(O)(=O)=O.[C:6]([O:13][CH3:14])(=[O:12])[CH2:7][C:8]([O:10][CH3:11])=[O:9].C(O)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C(O[C:35](=O)[CH3:36])C.[CH3:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]>ClCCl>[C:6]([O:13][CH2:14][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH3:16])(=[O:12])[CH2:7][C:8]([O:10][CH2:11][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:35][CH3:36])=[O:9]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 2682Cetyl AlcoholHCID 7943Dimethyl malonate2×HCID 21226206Ethyl acetate hexane

Product 1

HCID 219487dihexadecyl propanedioate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

H2SO4 (conc) (0.1 mL, 0.0036 mol % was slowly added to a mixture of dimethyl malonate (2 g, 0.015 mol) and hexadecanol (15 mL, 0.061 mol) and the mixture was heated at reflux until all dimethyl malonate was converted according to TLC (approximately 4 days). The product mixture was dissolved in dichloromethane (DCM), extracted with water (3 times) and dried over MgSO4. An analytically pure sample was obtained by column chromatography on silica gel using a 1:9 mixture of ethylacetate/hexane. Yield: 5.5 g (65.7%), see JP 57067510.

Workup

  1. temperaturethe mixture was heated
  2. customwas converted according to TLC (approximately 4 days)
  3. extractionextracted with water (3 times)
  4. dry with materialdried over MgSO4
  5. customAn analytically pure sample was obtained by column chromatography on silica gel using

Sources & evidence

ORD record
ord-a60e5b7ee8f84f738510cb7d0010cf7d
Source dataset
uspto-grants-2013_05
Patent number
US08435931B2

Reaction notes

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