Water → (2-Methoxy-6-methylphenyl)methanol

HRID 1157846

反応式

HRID 1157846 の反応式
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:4]=1[C:5](OCC)=[O:6].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C(OCC)C>[CH3:1][O:2][C:3]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:4]=1[CH2:5][OH:6]

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 5910602-Methoxy-6-methyl-benzoic acid ethyl esterHCID 21226445Aluminium lithium hydride

生成物 1

HCID 13208697(2-Methoxy-6-methylphenyl)methanol収率 99.7%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To a solution of ethyl 2-methoxy-6-methylbenzoate (1.23 g, 6.33 mmol) in dry diethyl ether (58 mL) was added LiAlH4 (0.467 g, 12.31 mmol) and the resultant mixture was heated to reflux for 2 hours then cooled to room temperature. The mixture was treated sequentially with water (0.45 mL), 15% aqueous NaOH (0.45 mL) and water (1.35 mL). The mixture was filtered through Celite© and the cake was washed with ether (200 mL). The filtrate was concentrated under reduced pressure and provided 0.96 g (99%) of 2-methoxy-6-methylbenzyl alcohol as a yellow solid. 1H NMR (CDCl3) δ 2.27 (t, 1H, J=6.3 Hz), 2.39 (s, 3H), 3.86 (s, 3H), 4.75 (d, 2H, J=6.3 Hz), 6.76 (d, 1H, J=8.4 Hz), 6.81 (d, 1H, J=7.8 Hz), 7.17 (dd, 1H, J=7.8, 8.4 Hz).

後処理

  1. temperatureto reflux for 2 hours
  2. filtrationThe mixture was filtered through Celite©
  3. washthe cake was washed with ether (200 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-a9fe6d4f523341b5b9de5ef8e830aad9
出典データセット
uspto-grants-2010_10
特許番号
US07807694B2

関連ノート

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