Hydrochloric Acid → 3,5-Diisopropoxybenzoic acid-1G

HRID 883829노트

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HRID 883829 반응식
C(OC1C=CC=CC=1C([O-])=O)(C)C.[CH:14]([O:17][C:18]1[CH:19]=[C:20]([CH:27]=[C:28]([O:30][CH:31]([CH3:33])[CH3:32])[CH:29]=1)[C:21]([O:23]C(C)C)=[O:22])([CH3:16])[CH3:15].[OH-].[Li+].Cl>C1COCC1.O>[CH:31]([O:30][C:28]1[CH:27]=[C:20]([CH:19]=[C:18]([O:17][CH:14]([CH3:16])[CH3:15])[CH:29]=1)[C:21]([OH:23])=[O:22])([CH3:33])[CH3:32]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 40493909IsopropoxybenzoateHCID 58261000Isopropyl 3,5-diisopropoxybenzoate

생성물 1

HCID 205341403,5-Diisopropoxybenzoic acid-1G수율 55%

시약·촉매·용매 1

HCID 21881883Oxolane--water (1/1)용매

실험 절차

Crude isopropoxybenzoate from above (compound E) was dissolved in 200 mL THF/H2O (1:1) in a 500 mL flask. Excess lithium hydroxide (10 g) was added and the reaction refluxed for over 48 hours. The mixture was cooled, acidified with HCl to pH 2, then extracted with several portions of diethyl ether. The organic layers were washed with brine, dried over MgSO4, and concentrated to a white solid in 55% yield over 2 steps: IR (cm−1): 3064, 2978, 2933, 2639, 1693, 1594, 1300, 1158, 1114, 1040, 767; 1H NMR (250 MHz, CD3OD): δ 1.30 (dd, J=2.3, 5.9 Hz, 12H), 4.59 (qn, J=6.2 Hz, 2H), 6.61 (t, J=2.3 Hz, 1H), 7.10 (d, J=2.5 Hz, 2H); 13C NMR (63 MHz, CD3OD): 22.2 (4C), 71.2 (2C), 109.8, 109.9, 133.8, 160.3 (2C), 169.7.

후처리

  1. temperaturethe reaction refluxed for over 48 hours
  2. temperatureThe mixture was cooled
  3. extractionextracted with several portions of diethyl ether
  4. washThe organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to a white solid in 55% yield over 2 steps

출처 및 근거

ORD 기록
ord-2f7927aeaf8d4a39baf3b92ea88b9f84
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08237003B2

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