Benzoic Acid → HCID 56984157, compound

HRID 1395214Notes

Reaction equation

HRID 1395214 reaction equation
[C:1]([CH:6]1[CH2:11][CH2:10][CH:9]([CH:12]=O)[CH2:8][CH2:7]1)([CH2:4][CH3:5])([CH3:3])[CH3:2].[C:14]([C:19](=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:20])([O:16][CH2:17][CH3:18])=[O:15].C(O)(=O)C1C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:17]([O:16][C:14](=[O:15])[C:19]([CH3:20])=[CH:12][CH:9]1[CH2:8][CH2:7][CH:6]([C:1]([CH2:4][CH3:5])([CH3:2])[CH3:3])[CH2:11][CH2:10]1)[CH3:18]

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 79792Ethyl 2-(triphenylphosphoranylidene)propionateHCID 203406004-Tert.amyl-cyclohexane-1-carboxaldehyde

Product 1

HCID 56984157HCID 56984157, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 46.3 g of 4-tert.amyl-cyclohexane-1-carboxaldehyde, 92.3 g of (α-carbethoxy-ethylidene)-triphenyl-phosphorane and 7.6 g of benzoic acid in 250 ml of toluene is heated at reflux for 3.5 hours under nirogen gasification and the toluene is evaporated. The oily-crystalline residue is dissolved in 1600 ml of methanol/water (4:1) and exhaustively extracted with hexane. The combined hexane extracts are washed with sodium carbonate solution and water, dried over sodium sulphate and evaporated. By distillation there is obtained pure 3-(4-tert.amyl-cyclohexyl)-2-methyl-acrylic acid ethyl ester of boiling point 113°-115° C./0.03 Torr.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 3.5 hours under nirogen gasification
  3. customthe toluene is evaporated
  4. dissolutionThe oily-crystalline residue is dissolved in 1600 ml of methanol/water (4:1)
  5. extractionexhaustively extracted with hexane
  6. washThe combined hexane extracts are washed with sodium carbonate solution and water
  7. dry with materialdried over sodium sulphate
  8. customevaporated
  9. distillationBy distillation there

Sources & evidence

ORD record
ord-b5aefe35b1e94d719a364b9f83476dfd
Source dataset
uspto-grants-1980_05
Patent number
US04202894

Reaction notes

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