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

HRID 1386

反応式

HRID 1386 の反応式
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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-71d8a412e47743ae868fcc2cf8c525e8
出典データセット
uspto-grants-1998_03
特許番号
US05723666

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