Potassium Hydroxide → 2-Hydroxy-5-isopropyl-4-(methoxymethyloxy)benzoic acid

HRID 1182809ノート

反応式

HRID 1182809 の反応式
[OH-].[K+].[OH:3][C:4]1[CH:13]=[C:12]([O:14][CH2:15][O:16][CH3:17])[C:11]([CH:18]([CH3:20])[CH3:19])=[CH:10][C:5]=1[C:6]([O:8]C)=[O:7]>CO.O>[OH:3][C:4]1[CH:13]=[C:12]([O:14][CH2:15][O:16][CH3:17])[C:11]([CH:18]([CH3:20])[CH3:19])=[CH:10][C:5]=1[C:6]([OH:8])=[O:7]

参加物

5

反応物 2

HCID 14797Potassium HydroxideHCID 58236463Methyl 2-hydroxy-5-isopropyl-4-(methoxymethyloxy)benzoate

生成物 1

HCID 582364622-Hydroxy-5-isopropyl-4-(methoxymethyloxy)benzoic acid収率 83.2%

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, 1 ml) was added to a mixture of methyl 2-hydroxy-5-isopropyl-4-(methoxymethyloxy)benzoate (508 mg, 2.0 mmol) in methanol (10 ml) and water (4 ml) and the mixture was stirred and held at reflux for 6 hours. Upon cooling to room temperature the organic solvent was removed in vacuo and the residue acidified by the addition of 2M hydrochloric acid (30 ml). The solid material was collected by suction filtration, rinsed with water (2×20 ml) and sucked dry under reduced pressure to afford 2-hydroxy-5-isopropyl-4-(methoxymethyloxy)benzoic acid (400 mg, 83%) as a colourless solid. 1H NMR (DMSO-d6) 13.60 (1H, br s), 11.30 (1H, br s), 7.58 (1H, s), 6.58 (1H, s), 5.30 (2H, s), 3.42 (3H, s), 3.15 (1H, m), 1.18 (6H, d). MS: [M+H]+ 241.

後処理

  1. temperatureat reflux for 6 hours
  2. customwas removed in vacuo
  3. additionthe residue acidified by the addition of 2M hydrochloric acid (30 ml)
  4. filtrationThe solid material was collected by suction filtration
  5. washrinsed with water (2×20 ml)
  6. customsucked dry under reduced pressure

出典と根拠

ORDレコード
ord-7a947698db4e46b694d526d81859e60d
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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