Hydrochloric Acid → 4-(2-Methoxyethoxy)-3-methylbenzoic acid

HRID 72925

반응식

HRID 72925 반응식
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:11].[OH-].C([P+](CCCC)(CCCC)CCCC)CCC.Br[CH2:31][CH2:32][O:33][CH3:34].Cl>C1COCC1>[CH3:34][O:33][CH2:32][CH2:31][O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:11]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 681384-Hydroxy-3-methylbenzoic acidHCID 809722-Bromoethyl methyl etherHCID 84487Phosphonium, tetrabutyl-, hydroxide (1:1)

생성물 1

HCID 585513704-(2-Methoxyethoxy)-3-methylbenzoic acid수율 6.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a solution of 4-hydroxy-3-methyl-benzoic acid (2.0 g, 13 mmol) in THF (24 mL) was added tetrabutylphosphonium hydroxide (18 mL of 40% w/v, 26 mmol). The reaction mixture was cooled to 0° C. and then 1-bromo-2-methoxy-ethane (1.8 g, 1.2 mL, 13 mmol) was added. The reaction mixture was allowed to warm to room temperature overnight. The reaction mixture was acidified using 1M HCl and the aqueous layer was extracted with ethyl acetate. The organics were dried over sodium sulfate and concentrated in vacuo to yield 4-(2-methoxyethoxy)-3-methylbenzoic acid (182 mg, 6%). ESI-MS m/z calc. 210.2. Found 209.2 (M-H)−; Retention time: 0.96 minutes (3 min run).

후처리

  1. temperatureto warm to room temperature overnight
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. dry with materialThe organics were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-5d725e47a55940a89ffe32a8dd1e32ff
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828996B2

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