Hydrochloric Acid → 4-Bromo-2-(hydroxymethyl)-6-methoxyphenol

HRID 655650

反応式

HRID 655650 の反応式
[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

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 2622385-Bromo-2-hydroxy-3-methoxybenzaldehydeHCID 4311764Sodium borohydride

生成物 1

HCID 8940924-Bromo-2-(hydroxymethyl)-6-methoxyphenol収率 100.4%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ccc54352225947aa9aa1a81d6c3026d5
出典データセット
uspto-grants-2011_12
特許番号
US08071600B2

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