Water → (1-Benzylcyclohex-2-en-1-yl)acetic acid

HRID 890922노트

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HRID 890922 반응식
[O-]Cl=O.[Na+].[OH2:5].[CH2:6]([C:13]1([CH2:19][CH:20]=[O:21])[CH2:18][CH2:17][CH2:16][CH:15]=[CH:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CS(C)=O.CCOCC>[CH2:6]([C:13]1([CH2:19][C:20]([OH:5])=[O:21])[CH2:18][CH2:17][CH2:16][CH:15]=[CH:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 22243087(1-Benzylcyclohex-2-en-1-yl)acetaldehydeHCID 23668197Sodium Chlorite

생성물 1

HCID 22243083(1-Benzylcyclohex-2-en-1-yl)acetic acid

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매2회HCID 3283Diethyl Ether용매

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온도
0 °C

실험 절차

To a mixture of NaH2PO4 (55.3 g), NaClO2 (36.3 g), DMSO (200 mL) and water (375 mL) was added a solution of 3-benzyl-3-formylmethylcyclohexene (57 g) in DMSO (150 mL) during a 3 hour period. After addition, the mixture was stirred overnight and diluted with ether (200 mL). This was extracted with saturated NaHCO3 (3×100 mL). The combined aqueous layer was cooled to 0° C. and acidified to PH=1 with conc. HCl. This was extracted with CH2Cl2 (3×300 mL). The combined organic layer was dried (Na2SO4) and the solvent was removed in vacuo. The residue was purified by column chromatography on silica gel to give the title compound as thick oil (50 g). MS (MH+=231).

후처리

  1. additionAfter addition
  2. extractionThis was extracted with saturated NaHCO3 (3×100 mL)
  3. extractionThis was extracted with CH2Cl2 (3×300 mL)
  4. dry with materialThe combined organic layer was dried (Na2SO4)
  5. customthe solvent was removed in vacuo
  6. customThe residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-de41880043ba495f9adf2ef3b9cf08ea
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07001898B2

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