Propylene Glycol → 1,3-Dioxolane, 2,4-dimethyl-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-

HRID 1091003Notes

Reaction equation

HRID 1091003 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:13]([C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22]([CH3:27])([CH3:26])[CH2:21][CH2:20][C:19]2([CH3:29])[CH3:28])(=[O:15])[CH3:14].[CH2:30](O)[CH:31]([OH:33])[CH3:32].C1(C)C=CC=CC=1>O>[CH3:14][C:13]1([C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[C:22]([CH3:27])([CH3:26])[CH2:21][CH2:20][C:19]3([CH3:29])[CH3:28])[O:33][CH:31]([CH3:32])[CH2:30][O:15]1

Participants

6

Reactant 4

HCID 1030Propylene GlycolHCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 27475621-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-one

Product 1

HCID 30342781,3-Dioxolane, 2,4-dimethyl-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

p-Toluenesulphonic acid monohydrate (2 g) is added to a suspension of 120 g (0.5 mol) of 6-acetyl-1,1,4,4-tetra-methyl-tetralin, 120 g (1.6 mol) of propylene glycol and 600 ml of toluene. The mixture is heated to 110° C. The reaction water is removed azeotropically within 5 hours. After cooling to room temperature the mixture is adjusted to pH 7.5 to 8 by the addition of 10% potassium hydroxide in ethanol. Thereupon, the mixture is filtered. The solvent is evaporated and the residual liquid is distilled under a vacuum, whereby there separate as the main product 123 g of 2.4-dimethyl-2-(1,1,4,4-tetramethyl-tetralin-6-yl)-1,3-dioxolane as a mixture of the boiling point is 112° C. at 0.5 mmHg; nD20 =1.5130. The product has a strong woody, animalic odour.

Workup

  1. customis removed azeotropically within 5 hours
  2. temperatureAfter cooling to room temperature the mixture
  3. additionis adjusted to pH 7.5 to 8 by the addition of 10% potassium hydroxide in ethanol
  4. filtrationThereupon, the mixture is filtered
  5. customThe solvent is evaporated
  6. distillationthe residual liquid is distilled under a vacuum, whereby
  7. customthere separate as the main product 123 g of 2.4-dimethyl-2-(1,1,4,4-tetramethyl-tetralin-6-yl)-1,3-dioxolane as a mixture of the boiling point is 112° C. at 0.5 mmHg

Sources & evidence

ORD record
ord-0c257c305f18468ca3bd229ee80451b6
Source dataset
uspto-grants-1992_01
Patent number
US05084440

Reaction notes

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