Toluene → 3-(4,4-Dimethyl-cyclohex-1-enyl)-propan-1-ol

HRID 585466

Reaction equation

HRID 585466 reaction equation
C([O:5][C:6](=O)[CH2:7][CH2:8][C:9]1[CH2:14][CH2:13][C:12]([CH3:16])([CH3:15])[CH2:11][CH:10]=1)CCC.C1(C)C=CC=CC=1.C[SiH](O)C.C[Si](C)(C)C.C[Si](O)(C)C.[OH-].[K+]>[Zn+2].C(C(CC)C([O-])=O)C.C(C(CC)C([O-])=O)C.CO>[CH3:15][C:12]1([CH3:16])[CH2:13][CH2:14][C:9]([CH2:8][CH2:7][CH2:6][OH:5])=[CH:10][CH2:11]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 14797Potassium HydroxideHCID 16211393Methyl hydrogen polysiloxaneHCID 236558383-(4,4-Dimethyl-cyclohex-1-enyl)-propionic acid butyl ester

Product 1

HCID 223368773-(4,4-Dimethyl-cyclohex-1-enyl)-propan-1-olYield 89%

Reagents, catalysts & solvents 2

HCID 22336878Diethylacetate ZINCCatalystHCID 887MethanolSolvent

Procedure

3-(4,4-Dimethyl-cyclohex-1-enyl)-propionic acid butyl ester (277.0 g, 1.10 mol, purity: 95%), toluene (140 g) and diethylacetate zinc complex (13.85 g, 5% w/w ester) were charged in a 2 1 reactor. The pot temperature was risen to 105° C. and PMHS (Polymethylhydroxysilane, 149.0 g, 2.48 mol) was introduced over the course of 3 hours. Stirring was continued for 1 hour and then the pot temperature was decreased to 40° C. The reaction mixture was put in a dropping funnel and the 2 1 reactor charged with 45% w/w aqueous KOH (403 g, 3.23 mol) and methanol (64.0 g). The pot temperature was risen to 60° C. and the reaction mixture was introduced over 30 minutes. Stirring was continued for 2 hours. The aqueous phase was separated and the organic phase washed with 5% w/w aqueous NaCl and twice with water. After concentration of the organic layer, the crude product was flash distilled (81° C., 1 hPa) to give 164.8 g of the desired alcohol (yield: 85%; GC purity: 96.2%).

Workup

  1. customwas risen to 105° C.
  2. customwas decreased to 40° C
  3. customThe reaction mixture was put in a dropping funnel
  4. customwas risen to 60° C.
  5. additionthe reaction mixture was introduced over 30 minutes
  6. stirringStirring
  7. waitwas continued for 2 hours
  8. customThe aqueous phase was separated
  9. washthe organic phase washed with 5% w/w aqueous NaCl and twice with water
  10. distillationdistilled (81° C., 1 hPa)

Sources & evidence

ORD record
ord-97543e20fc9040729affef28d103d8bb
Source dataset
uspto-grants-2005_08
Patent number
US06933265B2

Linked notes

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