p-Toluenesulfonic acid → HCID 13561254, compound

HRID 704288Notes

Reaction equation

HRID 704288 reaction equation
[CH3:1][C:2]1([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:7][CH2:6][CH:5]([C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.C(C1CCC(C2C=CC=CC=2)CC1)#N.[Li+].CC([N-]C(C)C)C.C(Br)CCCCCC.CC(C[AlH]CC(C)C)C.NN.[CH2:62]([CH:68]([CH2:71]O)[CH2:69][OH:70])[CH2:63][CH2:64][CH2:65][CH2:66][CH3:67].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.O>[CH3:1][C:2]1([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:7][CH2:6][CH:5]([C:8]2[CH:9]=[CH:10][C:11]([CH:12]3[O:70][CH2:69][CH:68]([CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH3:67])[CH2:71][O:13]3)=[CH:14][CH:15]=2)[CH2:4][CH2:3]1

Participants

11

Reactant 8

HCID 6101p-Toluenesulfonic acidHCID 9321HydrazineHCID 123691-BromoheptaneHCID 14487Diisobutylaluminum hydrideHCID 2684842-Hexylpropane-1,3-diolHCID 2724682Lithium diisopropylamideHCID 1356125032274-07-0HCID 13561253HCID 13561253, compound

Product 1

HCID 13561254HCID 13561254, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

27.2 g (0.1 mole) of p-(4-methyl-4-pentylcyclohexyl)-benzaldehyde (obtainable from 4-cyanocyclohexylbenzene by alkylation with LDA and heptyl bromide, stepwise conversion of the nitrile group into the methyl group by reduction with DIBAH and hydrazine in a Wolff-Kishner reaction and introduction of the formyl group by chloromethylation and a Sommelet reaction) are boiled with 16.0 g (0.1 mole) of 2-hexylpropane-1,3-diol and 0.1 g of p-toluenesulfonic acid in 150 ml of toluene, using a water separator, until no further water of reaction is formed. The cooled reaction mixture is washed twice with 5% NaHCO3 solution (100 ml each time) and then with water and dried. After the solvent has been evaporated off, the residue is recrystallised from ethanol. p-(4-Methyl-4-pentylcyclohexyl)-(5-hexyl-1,3-dioxan-2-yl)-benzene is obtained.

Workup

  1. customa Sommelet reaction)
  2. customis formed
  3. customThe cooled reaction mixture
  4. washis washed twice with 5% NaHCO3 solution (100 ml each time)
  5. dry with materialwith water and dried
  6. customAfter the solvent has been evaporated off
  7. customthe residue is recrystallised from ethanol

Sources & evidence

ORD record
ord-30f17a1f29ea454db7aeb269ca74949e
Source dataset
uspto-grants-1991_01
Patent number
US04985583

Reaction notes

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