Potassium Hydroxide → 2,4-Bis-allyloxy-5-isopropylbenzoic acid

HRID 1182805노트

반응식

HRID 1182805 반응식
[OH-].[K+].[CH2:3]([O:6][C:7]1[CH:16]=[C:15]([O:17][CH2:18][CH:19]=[CH2:20])[C:14]([CH:21]([CH3:23])[CH3:22])=[CH:13][C:8]=1[C:9]([O:11]C)=[O:10])[CH:4]=[CH2:5]>CO.O>[CH2:3]([O:6][C:7]1[CH:16]=[C:15]([O:17][CH2:18][CH:19]=[CH2:20])[C:14]([CH:21]([CH3:23])[CH3:22])=[CH:13][C:8]=1[C:9]([OH:11])=[O:10])[CH:4]=[CH2:5]

참가 물질

5

반응물 2

HCID 14797Potassium HydroxideHCID 58236457Methyl 2,4-bis-allyloxy-5-isopropylbenzoate

생성물 1

HCID 582364592,4-Bis-allyloxy-5-isopropylbenzoic acid수율 98%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

Aqueous potassium hydroxide (50% w/v, 0.5 ml) was added to a mixture of methyl 2,4-bis-allyloxy-5-isopropylbenzoate (450 mg, 1.55 mmol) in methanol (6 ml) and water (2 ml) and the mixture was stirred and held at reflux for 3 hours. Upon cooling to room temperature the organic solvent was removed in vacuo and the residue acidified by the addition of 2M hydrochloric acid (10 ml). The solid material was collected by suction filtration, rinsed with water (2×10 ml) and sucked dry under reduced pressure to afford 2,4-bis-allyloxy-5-isopropylbenzoic acid (418 mg, 98%) as an off-white solid. 1H NMR (DMSO-d6) 12.16 (1H, br s), 7.58 (1H, s), 6.66 (1H, s), 6.07 (2H, m), 5.51 (1H, dm), 5.44 (1H, dm), 5.28 (2H, m), 4.68 (2H, m), 4.64 (2H, m), 3.17 (1H, m), 1.15 (6H, d). MS: [M+Na]+ 299.

후처리

  1. temperatureat reflux for 3 hours
  2. customwas removed in vacuo
  3. additionthe residue acidified by the addition of 2M hydrochloric acid (10 ml)
  4. filtrationThe solid material was collected by suction filtration
  5. washrinsed with water (2×10 ml)
  6. customsucked dry under reduced pressure

출처 및 근거

ORD 기록
ord-2c4af7d6694e4132b757f5e89a326bb2
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08664218B2

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