Phosphoric Acid → 2,4-Dimethylresorcinol

HRID 975230

반응식

HRID 975230 반응식
[OH:1][C:2]1[C:9]([CH3:10])=[C:8]([OH:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.P(=O)(O)(O)O>[Pd].C(O)(C)C>[CH3:10][C:9]1[C:2]([OH:1])=[C:3]([CH3:4])[CH:6]=[CH:7][C:8]=1[OH:11]

참가 물질

5

반응물 2

HCID 1004Phosphoric AcidHCID 803952,4-Dihydroxy-3-methylbenzaldehyde

생성물 1

HCID 694522,4-Dimethylresorcinol수율 72%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 3776Isopropanol용매

실험 절차

A solution of 2,4-dihydroxy-3-methylbenzaldehyde (30.0 g, 197 mmol) with isopropanol (3 L) was ice-cooled in a 5 L 3-neck flask fitted with a magnetic stirrer. Phosphoric acid (4 mL) and 10% palladium on carbon were added and the solution was sparged with nitrogen, then hydrogen. When uptake was judged to be complete (c. 1.5 hour) the solution was again sparged with nitrogen and then filtered through Celite®. The solvent was stripped off, the residue taken up in ethyl acetate, and the resulting solution washed with water (4×100 mL). The water washes were back-extracted with ethyl acetate and the combined organic layers dried over sodium sulfate and stripped down. Sublimation (95°, 0.05 torr) afforded a colorless solid (19.6 g, 72%). M.p. 107°-8° C. (Lit. 108°-109° C. [W. Baker et al., J. Chem. Soc., 2834-5 (1949).]). NMR (DMSO-d6): δ1.969 (s, 3H), 2.037 (s, 3H), 6.220 (d, J=8.1 hz, 1H), 6.637 (d, J=8.1 hz, 1H), 7.929 (s, 1H), and 8.785 (s, 1H).

후처리

  1. temperaturecooled in a 5 L 3-neck flask
  2. customfitted with a magnetic stirrer
  3. customthe solution was sparged with nitrogen
  4. custom(c. 1.5 hour)
  5. customwas again sparged with nitrogen
  6. filtrationfiltered through Celite®
  7. washthe resulting solution washed with water (4×100 mL)
  8. extractionThe water washes were back-extracted with ethyl acetate
  9. dry with materialthe combined organic layers dried over sodium sulfate

출처 및 근거

ORD 기록
ord-63f6af3d4adc4e978ec2ca8ea7f5a509
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05608063

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