Stearic Acid → HCID 56638907, compound

HRID 2188356Notes

Reaction equation

HRID 2188356 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[C:10]([O:29]C)(=O)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]C.[CH3:31]C(C)([O-])C.[Na+].C(O)(=O)CCCCCCCCCCCCCCCCC>C1(C(C)C)C=CC=CC=1>[C:1]([CH2:2][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:10]([CH3:31])=[O:29])(=[O:3])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 5281Stearic AcidHCID 7410Acetophenone2×HCID 8201Methyl Stearate2×HCID 23676156Sodium t-butoxide

Product 1

HCID 56638907HCID 56638907, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 7406CumeneSolvent

Procedure

In a procedure analogous to Example 6, acetophenone was condensed with methyl stearate in cumene using sodium tert-butoxide (15.6 g, 0.163 mol). The acetophenone (15.0 g; 0.125 mol) was added over a period of 28 min, and no methanol was removed from the mixture by distillation. Crude SBM (44.76 g) was obtained. This crude was not purified by crystallization. It was possible, however, to quantitate the amount of SBM present by running a proton NMR spectrum at 54° C. of a sample dissolved in deuterated methanol. The total amount of SBM in the product was 32.65 g, that is, 73% of the sample, corresponding to a yield of 67% for the condensation. The impurities mainly comprised stearic acid and unreacted methyl stearate.

Workup

  1. customno methanol was removed from the mixture by distillation
  2. customCrude SBM (44.76 g) was obtained
  3. customThis crude was not purified by crystallization
  4. customat 54° C.
  5. dissolutiondissolved in deuterated methanol
  6. custom73% of the sample, corresponding to a yield of 67% for the condensation

Sources & evidence

ORD record
ord-aded4948576d4a79b080540756444248
Source dataset
uspto-grants-2002_06
Patent number
US06410795B1

Reaction notes

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