Hydrochloric Acid → 3-Cyclohexylacrylic acid

HRID 1512182Notes

Reaction equation

HRID 1512182 reaction equation
[C:1](O)(=O)[CH2:2][C:3]([OH:5])=[O:4].[CH:8]1(C=O)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.N1CCCCC1.Cl>N1C=CC=CC=1.O>[CH:8]1([CH:1]=[CH:2][C:3]([OH:5])=[O:4])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 16275Cyclohexanecarboxaldehyde

Product 1

HCID 2873483-Cyclohexylacrylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A solution of malonic acid (30 g, 0.29 mol), cyclohexanecarbaldehyde (17.3 ml, 0.14 mol) and piperidine (2.9 ml, 0.029 mol) in pyridine (90 ml) was stirred at 70° C. for 18 h. The resulting solution was allowed to cool to room temperature and then water (200 ml) was added. The resulting solution was acidified to pH 2 (litmus) using 1N HCl. The acidic aqueous solution was extracted thrice with ethyl acetate. The ethyl acetate extracts were pooled, washed successively with water, brine, dried over sodium sulfate, filtered and concentrated to yield 3-cyclohexyl-acrylic acid.

Workup

  1. extractionThe acidic aqueous solution was extracted thrice with ethyl acetate
  2. washwashed successively with water, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9dc19561e4f542729281dddec5de494f
Source dataset
uspto-grants-2012_07
Patent number
US08217060B2

Reaction notes

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