Water → [3,4-Bis(methoxymethoxy)]phenacyl chloride

反応式

[Cl:1][CH2:2][C:3]([C:5]1[CH:6]=[C:7]([OH:12])[C:8](=[CH:10][CH:11]=1)[OH:9])=[O:4].Cl[CH2:14][O:15][CH3:16].C(N(CC)CC)C.O.[O:25]1[CH2:29]CC[CH2:26]1>>[CH3:14][O:15][CH2:16][O:12][C:7]1[CH:6]=[C:5]([CH:11]=[CH:10][C:8]=1[O:9][CH2:26][O:25][CH3:29])[C:3](=[O:4])[CH2:2][Cl:1]

参加物

反応物 5

HCID 962Water

HCID 7864Chloromethyl Methyl Ether

HCID 8028Tetrahydrofuran

HCID 8471Triethylamine

HCID 668342-Chloro-3',4'-dihydroxyacetophenone

生成物 1

HCID 18367805[3,4-Bis(methoxymethoxy)]phenacyl chloride収率 78%

実験手順

4-(Chloroacetyl)catechol (4.1 g, 22 mmol), chloromethylmethylether (3.7 ml, 44 mmol) and triethylamine (12 ml) in tetrahydrofuran (50 ml) were stirred together for 1 h, the mixture poured into water (80 ml) and extracted with diethyl ether (80 ml×2). The organic extract was washed consecutively with 2N aqueous sodium hydroxide (50 ml×2) and water (50 ml), dried (MgSO4), and solvent evaporated to give 4.7 g (78%) of the title compound as a pale brown solid. (The crude product was used in the next step without further purification.)