Acrylic Acid → 3-Cyclohexene-1-carboxylic acid

HRID 1816082Notes

Reaction equation

HRID 1816082 reaction equation
C1([C:7]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:8])C=CC=CC=1.C=CC=C.C(O)(=[O:22])C=C>C1C=CC=CC=1>[CH:9]1([C:7]([OH:22])=[O:8])[CH2:14][CH2:13][CH:12]=[CH:11][CH2:10]1

Participants

5

Reactant 3

HCID 6581Acrylic Acid2×HCID 78451,3-Butadiene2×HCID 12837Cyclohexyl phenyl ketone

Product 1

HCID 209033-Cyclohexene-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The present invention relates to a method for preparing a cyclohexyl phenyl ketone from a 1,3 butadiene and acrylic acid without a purification or separation step and, more particularly, to a synthesis method of cyclohexyl phenyl ketone that includes carrying out a [2+4] Diels-Alder reaction of 1,3-butadiene and acrylic acid in the presence or absence of benzene or a non-aromatic organic solvent to yield 3-cyclohexene-1-carboxylic acid, a hydrogenation reaction to yield cyclohexanecarboxylic acid, a chlorination reaction to prepare a cyclohexanecarbonyl chloride; and a Friedel-Crafts reaction in the same reactor without purifying or separating the cyclohexanecarboxylic acid to prepare a cyclohexyl phenyl ketone with a high yield.

Workup

  1. customwithout a purification or separation step
  2. custommore particularly, to a synthesis method of cyclohexyl phenyl ketone that

Sources & evidence

ORD record
ord-848d5de8ad834ef180ab351db2b2f20b
Source dataset
uspto-grants-2005_04
Patent number
US06881865B2

Reaction notes

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