Benzoic Acid → 3-(4-Tert.butyl-cyclohexyl)-2-methyl-acrylic acid ethyl ester

HRID 1733275Notes

Reaction equation

HRID 1733275 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([CH:11]=O)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[C:13]([C:18](=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:19])([O:15][CH2:16][CH3:17])=[O:14].C(O)(=O)C1C=CC=CC=1>C1(C)C=CC=CC=1.CO.O>[CH2:16]([O:15][C:13](=[O:14])[C:18]([CH3:19])=[CH:11][CH:8]1[CH2:7][CH2:6][CH:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:10][CH2:9]1)[CH3:17]

Participants

6

Reactant 3

HCID 243Benzoic AcidHCID 79792Ethyl 2-(triphenylphosphoranylidene)propionateHCID 88655Cyclohexanecarboxaldehyde, 4-(1,1-dimethylethyl)-

Product 1

HCID 569892053-(4-Tert.butyl-cyclohexyl)-2-methyl-acrylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 22242641Methanol--water (1/1)Solvent

Procedure

A mixture of 20.2 g of 4-tert.butyl-cyclohexane-1-carboxaldehyde, 52 g of (α-carbethoxy-ethylidene)-triphenyl-phosphorane and 3.6 g of benzoic acid in 120 ml of toluene is heated at reflux for 16 hours under nitrogen gasification and the toluene is evaported. The oily-crystalline residue is dissolved in 600 ml of methanol/water (4:1) and exhaustively extracted with hexane. The combined hexane extracts are washed with sodium bicarbonate solution and water, dried over sodium sulphate and evaporated. By distillation there is obtained pure 3-(4-tert.butyl-cyclohexyl)-2-methyl-acrylic acid ethyl ester of boiling point 99° C./0.03 Torr.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 16 hours under nitrogen gasification
  3. extractionexhaustively extracted with hexane
  4. washThe combined hexane extracts are washed with sodium bicarbonate solution and water
  5. dry with materialdried over sodium sulphate
  6. customevaporated
  7. distillationBy distillation there

Sources & evidence

ORD record
ord-371e8a1fcf7f4418af5fe2f16400894e
Source dataset
uspto-grants-1980_12
Patent number
US04241058

Reaction notes

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