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

HRID 1386

반응식

HRID 1386 반응식
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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-71d8a412e47743ae868fcc2cf8c525e8
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05723666

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