Hydrogen Bromide → Bis(4-hydroxyphenyl)-2,4,5-trimethylphenylphosphine oxide

反応式

C[O:2][C:3]1[CH:8]=[CH:7][C:6]([P:9]([C:19]2[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=2)[C:10]2[CH:15]=[C:14]([CH3:16])[C:13]([CH3:17])=[CH:12][C:11]=2[CH3:18])=[CH:5][CH:4]=1.Br.[K+].[Br-].S([O-])([O-])=[O:31].[Na+].[Na+].CBr>>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([P:9](=[O:31])([C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)[C:10]2[CH:15]=[C:14]([CH3:16])[C:13]([CH3:17])=[CH:12][C:11]=2[CH3:18])=[CH:5][CH:4]=1

参加物

反応物 5

HCID 260Hydrogen Bromide

HCID 6323Methyl Bromide

HCID 24437Sodium Sulfite

HCID 253877Potassium Bromide

HCID 22290119Bis(4-methoxyphenyl)-2,4,5-trimethylphenylphosphine

生成物 1

HCID 22290104Bis(4-hydroxyphenyl)-2,4,5-trimethylphenylphosphine oxide収率 68.9%

反応条件

温度: 118 °C

実験手順

A reaction flask containing the bis(4-methoxyphenyl)-2,4,5-trimethylphenylphosphine. oxide mixture (443.7 g) was charged with 48% aq. HBr (934 mL) and KBr (59.5 g). The flask was fitted with a sodium sulfite scrubber for containment of methyl bromide. The reaction mixture was heated to reflux (118° C.) and maintained at reflux until complete based on HPLC analysis. The molten product was worked up to give 283.3 g of bis(4-hydroxyphenyl)-2,4,5-trimethylphenylphosphine oxide mixture as a cream solid (68.9% yield). The ratio of products in the mixture based on 31P NMR was 39% tris(4-hydroxyphenyl)phosphine oxide, 49% bis(4-hydroxyphenyl)-2,4,5-trimethylphenylphosphine oxide, 11% di-2,4,5-trimethylphenyl-4-hydroxyphenylphosphine oxide, and 1% tris(2,4,5-triethylphenyl)phosphine oxide.

後処理

temperatureThe reaction mixture was heated
temperaturemaintained
temperatureat reflux

出典と根拠

ORDレコード: ord-15afbf861c13483a9053de3f02c9a87c
出典データセット: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US06955851B2

反応ノート

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