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

HRID 1182798노트

반응식

HRID 1182798 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7d5e6f08872947128b55ca4fade98d05
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08664218B2

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