Chloromethyl Methyl Ether → Methyl 2-hydroxy-5-isopropyl-4-(methoxymethyloxy)benzoate

HRID 1182798ノート

反応式

HRID 1182798 の反応式
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[C:9]([CH:13]([CH3:15])[CH3:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH3:22][O:23][CH2:24]Cl>C(#N)C>[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH2:22][O:23][CH3:24])[C:9]([CH:13]([CH3:15])[CH3:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

参加物

5

反応物 3

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 59167875Methyl 2,4-dihydroxy-5-isopropylbenzoate

生成物 1

HCID 58236463Methyl 2-hydroxy-5-isopropyl-4-(methoxymethyloxy)benzoate収率 80.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of methyl 2,4-dihydroxy-5-isopropylbenzoate (1.05 g, 5.0 mmol) and anhydrous potassium carbonate (828 mg, 6.0 mmol) in acetonitrile (25 ml) was treated with chloromethyl methyl ether (0.4 ml, 5.27 mmol) and the mixture was stirred at room temperature for 3 hours. The solvent was removed in vacuo and the residue treated with water (30 ml). The solid material was collected by suction filtration, rinsed with water (2×20 ml) and sucked dry under reduced pressure to afford methyl 2-hydroxy-5-isopropyl-4-(methoxymethyloxy)benzoate (1.02 g, 80%) as a colourless solid. 1H NMR (DMSO-d6) 10.61 (1H, br s), 7.58 (1H, s), 6.62 (1H, s), 5.30 (2H, s), 3.88 (3H, s), 3.42 (3H, s), 3.17 (1H, m), 1.17 (6H, d). MS: [M+H]+ 255.

後処理

  1. customThe solvent was removed in vacuo
  2. additionthe residue treated with water (30 ml)
  3. filtrationThe solid material was collected by suction filtration
  4. washrinsed with water (2×20 ml)
  5. customsucked dry under reduced pressure

出典と根拠

ORDレコード
ord-7d5e6f08872947128b55ca4fade98d05
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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