Hydrochloric Acid → Adamantane-1,4-diol

HRID 1752280

반응식

HRID 1752280 반응식
[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([C:5]3=[O:12])[CH2:3]1)[CH2:9]2.[BH4-].[Na+].Cl>CO.CCOC(C)=O>[C:2]12([OH:1])[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH:5]3[OH:12])[CH2:3]1)[CH2:9]2

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 64184IdramantoneHCID 4311764Sodium borohydride

생성물 1

HCID 4252005Adamantane-1,4-diol수율 41.9%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

A stirred solution of 1-hydroxy-4-adamantanone (10.53 g, 63.4 mmol) in MeOH (100 mL) was cooled in an ice bath and NaBH4 (5×1-g caplets, 5.0 g, 130 mmol) was added. The ice bath was allowed to melt and the mixture was stirred overnight. 5% aq HCl (25 mL) was added and the mixture was concentrated to leave a white solid. This material was suspended in EtOAc (350 mL) and 5% aq HCl (100 mL) and filtered. The organic layer of the filtrate was collected, washed with brine, dried over Na2SO4 and concentrated to afford 1,4-adamantanediol (4.47 g, 41%).

후처리

  1. concentrationthe mixture was concentrated
  2. customto leave a white solid
  3. filtration5% aq HCl (100 mL) and filtered
  4. customThe organic layer of the filtrate was collected
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-000f6b14666b42e087438394ec743a18
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09163012B2

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