Citric Acid → 1-Naphthaldehyde

HRID 352693

반응식

HRID 352693 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]1([CH2:21][OH:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1.CCN(CC)CC.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl.O>[C:11]1([CH:21]=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1

참가 물질

8

반응물 5

HCID 311Citric AcidHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 209081-NaphthalenemethanolHCID 65578Oxalyl chloride

생성물 1

HCID 61951-Naphthaldehyde수율 98.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

To a cold (−78° C.) solution of oxalyl chloride (6.9 mL, 0.079 mol) in dry CH2Cl2 (200 mL) was added dropwise dry DMSO 11.2 mL, 0.158 mol). The mixture was stirred for 10 min, and then a solution of 1-naphthalenemethanol (100 g, 0.063 mol) in dry CH2Cl2 (40 mL) was added over 15 min. The mixture was stirred for 10 min. and then Et3N (44 mL, 0.316 mol) was added slowly. The reaction mixture was allowed to warm to room temperature. After 3.5 h, to the pale yellow heterogeneous mixture was added 10% aqueous citric acid (30 mL) and water (100 mL). The organic phase was washed with water (100 mL) and saturated aqueous NaCl (100 mL), dried (anhydrous MgSO4), filtered, and concentrated. Ether-hexane (1:1) was added, and the mixture was filtered. Concentration provided a pale orange oil (9.7 g).

후처리

  1. stirringThe mixture was stirred for 10 min.
  2. waitAfter 3.5 h
  3. washThe organic phase was washed with water (100 mL) and saturated aqueous NaCl (100 mL)
  4. dry with materialdried (anhydrous MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. additionEther-hexane (1:1) was added
  8. filtrationthe mixture was filtered
  9. concentrationConcentration

출처 및 근거

ORD 기록
ord-5f47794c11b646ff894b8a88042ca0af
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06747150B2

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