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

HRID 965511Notes

Reaction equation

HRID 965511 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-003ffe5d2b64477e8c6e7147e64b968e
Source dataset
uspto-grants-1998_06
Patent number
US05773594

Reaction notes

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