Sulfuric Acid → 2,5-Bishydroxymethyl-4'-hexyloxybiphenyl

HRID 1635757노트

반응식

HRID 1635757 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:30]=[C:29]([C:31](OCC)=[O:32])[CH:28]=[CH:27][C:21]=2[C:22](OCC)=[O:23])=[CH:16][CH:15]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].S(=O)(=O)(O)O>C1COCC1>[OH:23][CH2:22][C:21]1[CH:27]=[CH:28][C:29]([CH2:31][OH:32])=[CH:30][C:20]=1[C:17]1[CH:18]=[CH:19][C:14]([O:13][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:15][CH:16]=1

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 11069361Diethyl 2-(4'-hexyloxyphenyl)terephthalateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 153765802,5-Bishydroxymethyl-4'-hexyloxybiphenyl

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

LiAlH4 (5.3 g, 140 mmol) and about 200 ml of THF were blanketed with argon in a reaction vessel and diethyl 2-(4′-hexyloxyphenyl)terephthalate (40 g, 100 mmol) (cf. C1) together with a further 50 ml of THF were slowly added dropwise from a dropping funnel. The reaction mixture was stirred vigorously during this addition. The mixture was subsequently refluxed for about one hour. The reaction mixture was brought to RT and, while cooling in a water bath and blanketing with argon, ice water was carefully added dropwise until gas evolution had ceased. Dilute (10% strength) sulfuric acid was subsequently added dropwise until the turbid gray mixture was clear. The phases were separated by addition of chloroform and the aqueous phase was shaken twice with chloroform. The organic phases were washed once with H2O and subsequently evaporated. The crude product obtained was recrystallized from hexanelethyl acetate (5:1).

후처리

  1. temperatureThe mixture was subsequently refluxed for about one hour
  2. customwas brought to RT
  3. temperaturewhile cooling in a water bath
  4. additionwas carefully added dropwise until gas evolution
  5. additionwas subsequently added dropwise until the turbid gray mixture
  6. customThe phases were separated by addition of chloroform
  7. stirringthe aqueous phase was shaken twice with chloroform
  8. washThe organic phases were washed once with H2O
  9. customsubsequently evaporated

출처 및 근거

ORD 기록
ord-b2047d0a6719455f8d39f22d6af8a163
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06509507B2

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