Ethylene Glycol → 6-(2-methyl-1,3-dioxolan-2-yl)3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one

HRID 24583Notes

Reaction equation

HRID 24583 reaction equation
CC1(C)C2C(=C[C:8]([C:12](=[O:14])C)=CC=2)C(=O)CC1.[CH3:17][C:18]1([CH3:32])[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([C:28](=[O:30])[CH3:29])[CH:26]=2)[C:21](=[O:31])[CH2:20][CH2:19]1.C(O)CO.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:29][C:28]1([C:25]2[CH:26]=[C:27]3[C:22](=[CH:23][CH:24]=2)[C:21](=[O:31])[CH2:20][CH2:19][C:18]3([CH3:32])[CH3:17])[O:14][CH2:12][CH2:8][O:30]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 111067823,4-dihydro-4,4-dimethyl-6-acetyl-1(2H)-naphthalenoneHCID 223237263,4-dihydro-4,4-dimethyl-7-acetyl-1(2H)-naphthalenone

Product 1

HCID 154628436-(2-methyl-1,3-dioxolan-2-yl)3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 1.80 g (8.34 mmol) of a 1:5 mixture of 3,4-dihydro-4,4-dimethyl-7-acetyl-naphthalen-1(2H)-one (Compound D14a); and 3,4-dihydro-4,4-dimethyl-6-acetyl-naphthalen-1(2H)-one (Compound D14b) in 50 mL benzene was combined with 517.7 mg (8.34 mmol) of ethylene glycol and 20.0 mg (0.11 mmol) of p-toluenesulfonic acid monohydrate. The resulting solution was heated to reflux for 18 h, cooled to room temperature, and concentrated under reduced pressure. The title compound was isolated by column chromatography (10% EtOAc-hexanes) as a colorless oil.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 18 h
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-88d6c087375b40c2afc32a6443537b9f
Source dataset
uspto-grants-2005_02
Patent number
US06855832B2

Reaction notes

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