Water → HCID 20402794, compound

HRID 1093911Notes

Reaction equation

HRID 1093911 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:7][CH:6]([CH3:8])[CH2:5][CH:4]([OH:9])[CH2:3]1.N1C=CC=CC=1.[C:17](Cl)(=[O:21])/[CH:18]=[CH:19]/[CH3:20].O>C(OC)(C)(C)C>[C:17]([O:9][CH:4]1[CH2:5][CH:6]([CH3:8])[CH2:7][C:2]([CH3:10])([CH3:1])[CH2:3]1)(=[O:21])/[CH:18]=[CH:19]/[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 82983,3,5-TrimethylcyclohexanolHCID 643131trans-Crotonyl chloride

Product 1

HCID 20402794HCID 20402794, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

71 g of 3,3,5-trimethylcyclohexanol having a cis content of 90% are placed in a 1-l reaction flask together with 60 g of pyridine in 300 ml of methyl tert-butyl ether and 63 g of crotonic acid chloride are added at 0 to 5° C. over 30 minutes. The reaction mixture is left to continue reacting for a further one hour at this temperature; it is then allowed to heat up to room temperature. After one hour it is heated for a further 30 min to 50° C. After cooling, it is fractionated with water, the organic phase is separated off and first washed with dilute hydrochloric acid and then stirred for a further 30 min with 5-percent sodium hydroxide solution. After washing until it is neutral, the solvent is drawn off and the residue distilled using a short column. 63 g of pure 3,3,5-trimethylcyclohexyl crotonate having a cis content of 90% are obtained at a boiling point of 121° C. under 20 mbar. MS: 210 (M*, 0,3), 195 (0,5), 141 (3), 124 (75), 109 (100), 95 (24), 87 (24), 82 (25), 69 (75), 55 (11), 41 (33). The cis-3,3,5-trimethylcyclohexyl esters of propionic acid, isobutyric acid and butyric acid can be prepared in an analogous manner.

Workup

  1. additionare added at 0 to 5° C. over 30 minutes
  2. waitThe reaction mixture is left
  3. temperatureAfter one hour it is heated for a further 30 min to 50° C
  4. temperatureAfter cooling
  5. customthe organic phase is separated off
  6. washfirst washed with dilute hydrochloric acid
  7. washAfter washing until it
  8. distillationthe residue distilled

Sources & evidence

ORD record
ord-207e70a28c2c4fc3b089894cf168c735
Source dataset
uspto-grants-2012_03
Patent number
US08133856B2

Reaction notes

Loading…