Benzene → 1-Allylcyclohexanecarbaldehyde

HRID 1099477Notes

Reaction equation

HRID 1099477 reaction equation
[CH:1]1([CH:7]=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:9](O)[CH:10]=[CH2:11].C1C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH2:11]([C:1]1([CH:7]=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH:10]=[CH2:9]

Participants

6

Reactant 4

HCID 241BenzeneHCID 7858Allyl AlcoholHCID 16275CyclohexanecarboxaldehydeHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 118049631-AllylcyclohexanecarbaldehydeYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of cyclohexanecarboxaldehyde ((10 mL, 0.825 mol), allyl alcohol (60 mL, 98% purity, 0.882 mol), benzene (15 mL), and p-toluenesulfonic acid monohydrate (0.120 g, 0.63 mmol) was heated from 130° C. to 180° C. in an oil bath, under a Vigreaux distillation column, topped by a Dean-Stark trap. After 15 hour no more water was added over the 15 mL collected in the trap, and the reaction was judged completed. Subsequent distillation of the reaction crude gave 98 g (78% yield) of 1-allyl-cyclohexanecarboxaldehyde as a colourless liquid (b.p. 69-71° C./5 mm Hg).

Workup

  1. temperaturewas heated from 130° C. to 180° C. in an oil bath, under a Vigreaux distillation column
  2. customcollected in the trap
  3. distillationSubsequent distillation of the reaction crude

Sources & evidence

ORD record
ord-a3eef575d734412ca41ad26a11cddb98
Source dataset
uspto-grants-2012_03
Patent number
US08143443B2

Reaction notes

Loading…