Potassium Hydroxide → 2,4-Bis-allyloxy-5-isopropylbenzoic acid

HRID 1182805ノート

反応式

HRID 1182805 の反応式
[OH-].[K+].[CH2:3]([O:6][C:7]1[CH:16]=[C:15]([O:17][CH2:18][CH:19]=[CH2:20])[C:14]([CH:21]([CH3:23])[CH3:22])=[CH:13][C:8]=1[C:9]([O:11]C)=[O:10])[CH:4]=[CH2:5]>CO.O>[CH2:3]([O:6][C:7]1[CH:16]=[C:15]([O:17][CH2:18][CH:19]=[CH2:20])[C:14]([CH:21]([CH3:23])[CH3:22])=[CH:13][C:8]=1[C:9]([OH:11])=[O:10])[CH:4]=[CH2:5]

参加物

5

反応物 2

HCID 14797Potassium HydroxideHCID 58236457Methyl 2,4-bis-allyloxy-5-isopropylbenzoate

生成物 1

HCID 582364592,4-Bis-allyloxy-5-isopropylbenzoic acid収率 98%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

Aqueous potassium hydroxide (50% w/v, 0.5 ml) was added to a mixture of methyl 2,4-bis-allyloxy-5-isopropylbenzoate (450 mg, 1.55 mmol) in methanol (6 ml) and water (2 ml) and the mixture was stirred and held at reflux for 3 hours. Upon cooling to room temperature the organic solvent was removed in vacuo and the residue acidified by the addition of 2M hydrochloric acid (10 ml). The solid material was collected by suction filtration, rinsed with water (2×10 ml) and sucked dry under reduced pressure to afford 2,4-bis-allyloxy-5-isopropylbenzoic acid (418 mg, 98%) as an off-white solid. 1H NMR (DMSO-d6) 12.16 (1H, br s), 7.58 (1H, s), 6.66 (1H, s), 6.07 (2H, m), 5.51 (1H, dm), 5.44 (1H, dm), 5.28 (2H, m), 4.68 (2H, m), 4.64 (2H, m), 3.17 (1H, m), 1.15 (6H, d). MS: [M+Na]+ 299.

後処理

  1. temperatureat reflux for 3 hours
  2. customwas removed in vacuo
  3. additionthe residue acidified by the addition of 2M hydrochloric acid (10 ml)
  4. filtrationThe solid material was collected by suction filtration
  5. washrinsed with water (2×10 ml)
  6. customsucked dry under reduced pressure

出典と根拠

ORDレコード
ord-2c4af7d6694e4132b757f5e89a326bb2
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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