HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sulfuric Acid → 6-Isopropyl-2-methyl-3-cyclohexene-1-carboxylic acid

HRID 1905352
Notes
Print preview

Reaction equation

HRID 1905352 reaction equation
[CH3:1][CH:2]([CH3:8])/[CH:3]=[CH:4]/[C:5]([OH:7])=[O:6].[CH2:9]=[CH:10][CH:11]=[CH:12][CH3:13].CC(C)C=CC(O)=O.S(=O)(=O)(O)O>CCOCC>[CH:2]([CH:3]1[CH:4]([C:5]([OH:7])=[O:6])[CH:12]([CH3:13])[CH:11]=[CH:10][CH2:9]1)([CH3:8])[CH3:1]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 15301Penta-1,3-diene2×HCID 1121034-Methyl-pent-2-enoic acid2×HCID 6420393-Isopropyl acrylic acid

Product 1

HCID 200354126-Isopropyl-2-methyl-3-cyclohexene-1-carboxylic acidYield 65.7%

Reagents, catalysts & solvents 1

HCID 3283
Diethyl Ether
Solvent

Conditions

Temperature
200 °C

Procedure

A mixture of 70 g (0.61 mol) of trans-4-methyl-2-pentenoic acid and 49 g (0.72 mol) of 1,3-pentadiene was heated for 12 hours at approx. 200° C. in an autoclave. After the reaction mixture had cooled, it was checked by means of GLC for the presence of 4-methyl-2-pentenoic acid. A further 25 g (0.36 mol) of 1,3-pentadiene were added, after which the mixture was again heated for 12 hours at 200° C. This procedure was repeated until no further decrease in the content of 4-methyl-2-pentenoic acid was any longer observed. The reaction mixture obtained was dissolved in 300 ml of ether and extracted with 300 ml of 10% NaOH solution. The alkaline solution thus obtained was acidified with 40 g of concentrated sulphuric acid and then extracted three times with ether. The ether extract was washed with water, dried on MgSO4, evaporated down and distilled. 73 g of 6-isopropyl-2-methyl-3-cyclohexene-1-carboxylic acid were obtained, b.p.: 95°-100° C./70 Pa.

Workup

  1. temperatureAfter the reaction mixture had cooled
  2. temperatureafter which the mixture was again heated for 12 hours at 200° C
  3. customThe reaction mixture obtained
  4. extractionextracted with 300 ml of 10% NaOH solution
  5. customThe alkaline solution thus obtained
  6. extractionextracted three times with ether
  7. extractionThe ether extract
  8. washwas washed with water
  9. customdried on MgSO4
  10. customevaporated down
  11. distillationdistilled

Sources & evidence

ORD record
ord-34827857b5414388885e7bf4867918d7
Source dataset
uspto-grants-1989_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04843061

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes