Acetic Acid → HCID 21839221, compound

HRID 1681230Notes

Reaction equation

HRID 1681230 reaction equation
CC([O:5][C:6](=[O:29])[CH:7]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:8]([O:10]C(C)(C)C)=[O:9])(C)C.CC([O-])(C)C.[K+].[C:36]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)(=[O:39])[CH:37]=[CH2:38].CC(O)=O>CC(O)(C)C>[CH2:41]([O:40][C:36](=[O:39])[CH2:37][CH2:38][C:7]([C:8]([OH:10])=[O:9])([C:6]([OH:5])=[O:29])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 75617Benzyl acrylateHCID 21839216HCID 21839216, compoundHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 21839221HCID 21839221, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of di-(dimethylethyl)-n-tetradecylmalonate 34 (4.12 g, 10.0 mmol) and t-BuOK (244 mg, 2.0 mmol) in t-BuOH (10 mL, dried over 4 Å sieves) was added a solution of benzyl acrylate (1.62 g, 10.0 mmol in 5 mL t-BuOH). The initially colorless solution immediately turned brown. It was stirred (3 h, rt) then additional t-BuOK (112 mg, 1.0 mmol) was added and the reaction continued overnight. The mixture was neutralized with AcOH then evaporated to dryness and treated with neat TFA (20 mL, 1 h). The TFA was removed by rotary evaporation, the residue dissolved in warm hexane, treated with activated charcoal then filtered. The filtrate provided fine white crystals which proved to be pasty when filtered. Drying provided product 36 as a white solid (2.31 g, 50%), mp 47°-49° C. High resolution FAB MS:C27H43O6 (M+H); Theor. 463.307147. Found 463.3059 646. Anal. C27H42O6.1/2H2O:C,H.

Workup

  1. customthe reaction continued overnight
  2. customthen evaporated to dryness
  3. additiontreated with neat TFA (20 mL, 1 h)
  4. customThe TFA was removed by rotary evaporation
  5. dissolutionthe residue dissolved in warm hexane
  6. additiontreated with activated charcoal
  7. filtrationthen filtered
  8. customThe filtrate provided fine white crystals which
  9. filtrationfiltered
  10. customDrying

Sources & evidence

ORD record
ord-ad341a0166264629bbb9107ac273c2f7
Source dataset
uspto-grants-1992_12
Patent number
US05169862

Reaction notes

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