Hydrochloric Acid → [2-Bromo-5-(hydroxymethyl)phenyl]methanol

HRID 585336ノート

反応式

HRID 585336 の反応式
C([O:4][CH2:5][C:6]1[CH:11]=[C:10]([CH2:12][O:13]C(=O)C)[CH:9]=[CH:8][C:7]=1[Br:17])(=O)C.C(OCC1C=CC=C(COC(=O)C)C=1Br)(=O)C.[OH-].[Na+].Cl>CO.C1(C)C=CC=CC=1>[OH:4][CH2:5][C:6]1[CH:11]=[C:10]([CH2:12][OH:13])[CH:9]=[CH:8][C:7]=1[Br:17]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 99482912,4-Bis(acetoxymethyl)bromobenzeneHCID 223406402,6-Bis(acetoxymethyl)bromobenzene

生成物 1

HCID 12968884[2-Bromo-5-(hydroxymethyl)phenyl]methanol収率 83.9%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 1140Toluene溶媒

反応条件

温度
10 °C

実験手順

An about 93:7 mixture (36.7 g) of 2,4-bis(acetoxymethyl)-bromobenzene and 2,6-bis(acetoxymethyl)bromobenzene was dissolved in methanol (183 ml) and cooled to 10° C. To this solution was added dropwise 10% aqueous sodium hydroxide solution (133 g). The reaction mixture was stirred at room temperature for 1 hr, and the solvent (about 200 ml) was evanorated The residue was neutralized with dilute hydrochloric acid (about 200 ml). To the neutralized solution was added toluene (150 ml) and the mixture was stirred at 80-85° C. for 1 hr and cooled. The resulting crystals were collected by filtration and dried under reduced pressure to give an about 93:7 mixture (22.2 g, 83.7%) of 2,4-bis(hydroxymethyl)bromobenzene and 2,6-bis(hydroxymethyl)-bromobenzene as almost white crystals. 2,4-bis(Hydroxymethyl)-bromobenzene was isolated by preparative HPLC and used in the measurement.

後処理

  1. stirringthe mixture was stirred at 80-85° C. for 1 hr
  2. temperaturecooled
  3. filtrationThe resulting crystals were collected by filtration
  4. customdried under reduced pressure

出典と根拠

ORDレコード
ord-b2db50ced2fa4bb6aa9273dd5fc22918
出典データセット
uspto-grants-2005_08
特許番号
US06930211B2

反応ノート

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