Allyl bromide → Methyl 2-allyloxy-5-isopropyl-4-(methoxymethyloxy)benzoate

HRID 1182799ノート

反応式

HRID 1182799 の反応式
[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][O:14][CH3:15])[C:9]([CH:16]([CH3:18])[CH3:17])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:25](Br)[CH:26]=[CH2:27]>C(#N)C>[CH2:27]([O:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][O:14][CH3:15])[C:9]([CH:16]([CH3:18])[CH3:17])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])[CH:26]=[CH2:25]

参加物

5

反応物 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 58236463Methyl 2-hydroxy-5-isopropyl-4-(methoxymethyloxy)benzoate

生成物 1

HCID 58236458Methyl 2-allyloxy-5-isopropyl-4-(methoxymethyloxy)benzoate収率 97.5%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of methyl 2-hydroxy-5-isopropyl-4-(methoxymethyloxy)benzoate (995 mg, 3.92 mmol) and anhydrous potassium carbonate (650 mg, 4.71 mmol) in acetonitrile (25 ml) was treated with allyl bromide (0.356 ml, 4.11 mmol) and the mixture was stirred and held at reflux for 16 hours. Upon cooling to room temperature the solvent was removed in vacuo, water (30 ml) was added and the organic material was extracted with dichloromethane (2×30 ml). The combined organic extracts were evaporated to dryness in vacuo to afford methyl 2-allyloxy-5-isopropyl-4-(methoxymethyloxy)benzoate (1125 mg, 97%) as pale yellow oil. 1H NMR (DMSO-d6) 7.58 (1H, s), 6.78 (1H, s), 6.03 (1H, m), 5.52 (1H, dm), 5.33 (2H, s), 5.28 (1H, dm), 4.61 (2H, m), 3.78 (3H, s), 3.42 (3H, s), 3.19 (1H, m), 1.18 (6H, d). MS: [M+Na]+ 317.

後処理

  1. temperatureat reflux for 16 hours
  2. customwas removed in vacuo, water (30 ml)
  3. additionwas added
  4. extractionthe organic material was extracted with dichloromethane (2×30 ml)
  5. customThe combined organic extracts were evaporated to dryness in vacuo

出典と根拠

ORDレコード
ord-ba3561fd5e454a37954ac0ad0b083ed5
出典データセット
uspto-grants-2014_03
特許番号
US08664218B2

反応ノート

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