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

Hydrochloric Acid → 2,6-Dimethyl-2-(2-methyl-allyl)-cyclohexanone

HRID 61337
Notes
Print preview

Reaction equation

HRID 61337 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH3:8])[C:3]1=[O:9].C(OC)(OC)OC.Cl.[CH2:18](O)[C:19](=[CH2:21])[CH3:20].CS(O)(=O)=O>CC(O)=O.CO>[CH3:1][C:2]1([CH2:20][C:19]([CH3:21])=[CH2:18])[CH2:7][CH2:6][CH2:5][CH:4]([CH3:8])[C:3]1=[O:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6395Methanesulfonic AcidHCID 9005Trimethyl orthoformateHCID 10557Methallyl alcoholHCID 177802,6-Dimethylcyclohexanone

Product 1

HCID 897051892,6-Dimethyl-2-(2-methyl-allyl)-cyclohexanone

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

2,6-Dimethyl-cyclohexanone (1 kg, 4 mol), trimethyl orthoformate (TMOF, 880 g), and methanol (800 mL) were charged to a 5 L reaction flask. HCl was added quickly. Reaction exothermed and the temperature increased from 14° C. to 20° C. The reaction mixture was heated to 60° C. and aged for 7 hours. When the reaction was about 75% complete, the reaction mixture was quenched with NaOCH3 (25%, 25 g), heated to 90° C., and applied to a Bidwell-Sterling trap. The reaction mixture was then cooled to room temperature followed by sequential addition of methallyl alcohol (1.25 Kg, 8.5 moles), HOAc (50 g), and methane sulfonic acid (MSA, 10 g). The resulting mixture was heated to 110° C., applied to a Bidwell-Sterling trap, and aged for 4 hours until gas chromatograph analysis indicated that the reaction was 95% completed. The reaction mixture was then cooled and washed with saturated sodium carbonate solution (3 L) to provide the crude product 2,6-dimethyl-2-(2-methyl-allyl)-cyclohexanone.

Workup

  1. customReaction
  2. temperaturethe temperature increased from 14° C. to 20° C
  3. customthe reaction mixture was quenched with NaOCH3 (25%, 25 g)
  4. temperatureheated to 90° C.
  5. temperatureThe reaction mixture was then cooled to room temperature
  6. temperatureThe resulting mixture was heated to 110° C.
  7. temperatureThe reaction mixture was then cooled
  8. washwashed with saturated sodium carbonate solution (3 L)

Sources & evidence

ORD record
ord-f861df3ab22d4c698f270ecab7903ace
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09441185B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes