Hydrochloric Acid → Methyl 2-methoxymethoxy-3-n-propyl-4-methoxybenzoate

HRID 465911

반응식

HRID 465911 반응식
[K].[OH:2][C:3]1[C:12]([CH2:13][CH2:14][CH3:15])=[C:11]([O:16][CH3:17])[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].Cl[CH2:19][O:20][CH2:21]Cl.Cl>O1CCCC1>[CH3:19][O:20][CH2:21][O:2][C:3]1[C:12]([CH2:13][CH2:14][CH3:15])=[C:11]([O:16][CH3:17])[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 10967Bis(Chloromethyl) EtherHCID 5462222PotassiumHCID 14719500Methyl 2-hydroxy-3-n-propyl-4-methoxybenzoate

생성물 1

HCID 14719501Methyl 2-methoxymethoxy-3-n-propyl-4-methoxybenzoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

In argon atmosphere, a solution of potassium t-buthoxide (18.7 g) in tetrahydrofuran (200 ml) was cooled to 0° C., and to this solution was added dropwise a solution of methyl 2-hydroxy-3-n-propyl-4-methoxybenzoate (28 g) in tetrahydrofuran (100 ml) in 10 minutes, and the mixture was agitated for another 20 minutes. Chloromethyl ether (19.0 ml) was added thereto, and the mixture was agitated at 0° C. for 50 minutes. The reaction mixture was poured into 1N aqueous hydrochloric acid, and extracted twice with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, dried over anhydrous magnesium sulfate, and then concentrated in evacuated atomosphere. The residue was subjected to column chromatography using silica gel, and there was obtained methyl 2-methoxymethoxy-3-n-propyl-4-methoxybenzoate (29.9 g) from fractions eluted with n-hexane-ethyl acetate (10:1 to 5:1).

후처리

  1. stirringthe mixture was agitated at 0° C. for 50 minutes
  2. extractionextracted twice with ethyl acetate
  3. washThe organic layer was washed with saturated sodium bicarbonate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in evacuated atomosphere

출처 및 근거

ORD 기록
ord-21b4791723c5442387e74ec4867f2f03
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05155106

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