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

HRID 990174노트

반응식

HRID 990174 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) was added to about 200 ml of THF under a blanket of argon and diethyl 2-(4′-hexyloxyphenyl)terephthalate (40 9, 100 mmol) (cf. C1) together with a further 50 ml of THF was slowly added dropwise from a dropping funnel. The reaction mixture was vigorously stirred during this addition. It was subsequently refluxed for about one hour. The reaction mixture was brought to RT and, with water bath cooling and under a blanket of 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 with chloroform (twice). The organic phases were washed once with H2O and subsequently evaporated. The resulting crude product was recrystallized from hexane/ethyl acetate (5/1).

후처리

  1. additionwas slowly added dropwise from a dropping funnel
  2. temperatureIt was subsequently refluxed for about one hour
  3. customThe reaction mixture was brought to RT and, with 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 with chloroform (twice)
  8. washThe organic phases were washed once with H2O
  9. customsubsequently evaporated
  10. customThe resulting crude product was recrystallized from hexane/ethyl acetate (5/1)

출처 및 근거

ORD 기록
ord-7d1e84bb2f3f469d9418ede3451b387b
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06458909B1

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