海萝胶 → 4-溴-2-(羟基甲基)-6-甲氧基苯酚

HRID 655650

反应方程式

HRID 655650 反应方程式
[BH4-].[Na+].C1COCC1.[Br:8][C:9]1[CH:10]=[C:11]([O:18][CH3:19])[C:12]([OH:17])=[C:13]([CH:16]=1)[CH:14]=[O:15].Cl>C(O)(=O)C>[Br:8][C:9]1[CH:10]=[C:11]([O:18][CH3:19])[C:12]([OH:17])=[C:13]([CH2:14][OH:15])[CH:16]=1

参与物

6

反应物 4

HCID 313海萝胶HCID 8028四氢呋喃HCID 2622385-溴-2-羟基-3-甲氧基苯甲醛HCID 4311764硼氢化钠

产物 1

HCID 8940924-溴-2-(羟基甲基)-6-甲氧基苯酚收率 100.4%

试剂、催化剂与溶剂 1

HCID 176醋酸溶剂

反应条件

温度
0 °C

实验过程

Sodium borohydride (0.28 g, 6.9 mmol) was added to a THF solution (30 ml) of 5-bromo-2-hydroxy-3-methoxybenzaldehyde (3.2 g 13.8 mmol) under ice cooling and the mixture was stirred at 0° C. for 2 hours. Acetic acid was added to the reaction solution to set pH at 3. 10% hydrochloric acid was added to the reaction mixture, which was then extracted with ethyl acetate. The extracted material was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1→1:1) and concentrated to dryness under reduced pressure to obtain 4-bromo-2-hydroxymethyl-6-methoxyphenol (3.23 g) as light yellow oil.

后处理

  1. extractionwas then extracted with ethyl acetate
  2. dry with materialThe extracted material was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1→1:1)
  5. concentrationconcentrated to dryness under reduced pressure

来源与证据

ORD记录
ord-ccc54352225947aa9aa1a81d6c3026d5
来源数据集
uspto-grants-2011_12
专利号
US08071600B2

关联笔记

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