Hydrochloric Acid → 5,6-Dimethoxy-3H-isobenzofuran-1-one

HRID 571271

반응식

HRID 571271 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([OH:8])=[O:7].Cl.[CH2:15]=O>O>[CH3:13][O:12][C:11]1[CH:10]=[C:9]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[C:6](=[O:8])[O:7][CH2:15]2

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 7121Veratric Acid

생성물 1

HCID 2304605,6-Dimethoxy-3H-isobenzofuran-1-one수율 30%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A suspension of 3,4-dimethoxybenzoic acid (10 g, 54.9 mmol) in aqueous 37% HCl (126 ml, 1522 mmol) and a 37% solution in water of formaldehyde (25 ml, 54.9 mmol) were heated to 90 to 100° C. for 6 hours. Stirring was prolonged overnight at room temperature, and then the obtained insoluble material was removed by filtration. The filtrate was quenched with water (200 ml) and extracted with ethyl acetate (200 ml×3). The combined organic layers were washed with aqueous 1N NaOH (100 ml) and then with brine (2×100 ml). The organic phase was dried over Na2SO4, filtered and evaporated to dryness. The obtained yellow solid was triturated with ethyl acetate to afford 5,6-dimethoxyisobenzofuran-1(3H)-one as a white solid (3.171 g, 16.33 mmol, 30% yield). MS/ESI+ 195.0 [MH]+.

후처리

  1. customthe obtained insoluble material was removed by filtration
  2. customThe filtrate was quenched with water (200 ml)
  3. extractionextracted with ethyl acetate (200 ml×3)
  4. washThe combined organic layers were washed with aqueous 1N NaOH (100 ml)
  5. dry with materialThe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe obtained yellow solid was triturated with ethyl acetate

출처 및 근거

ORD 기록
ord-ffdae374dde9431eab5bf146c727c7e1
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09024027B2

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