Acetyl chloride → 1-Acetoxy-2-methylnaphthalene

HRID 260615

반응식

HRID 260615 반응식
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[OH:12].C(N(CC)CC)C.[C:20](Cl)(=[O:22])[CH3:21]>C(OCC)(=O)C>[C:20]([O:12][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]=1[CH3:1])(=[O:22])[CH3:21]

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 240552-Methyl-1-naphthol

생성물 1

HCID 118057271-Acetoxy-2-methylnaphthalene수율 63.1%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

실험 절차

A solution of 9.48 g (60 mmole) of 2-methyl-1-naphthol and 8.10 g (80 mmole) of triethylamine in 50 mL of ethyl acetate was cooled to below 5° C. in an ice-bath. 5.50 g (70 mmole) of acetyl chloride was added at a rate such that the temperature did not rise about 5° C. The reaction mixture was stirred for an additional one hour, diluted with 50 mL of ethyl acetate, and washed with water then brine. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated to give an oily residue. Crystallization in hexane yielded 7.58 g (63% yield) of the title compound with a melting point of 81°-83° C. and an 1HNMR as follows: (300 MHz, DMSO-d6) δ 2.26 ) (s, 3H), 2.48 (s, 3H), 7.42 (d, 1H, J=9 Hz), 7.46-7.55 (m, 2H), 7.47-7.81 (m, 2H), 7.92 (d, 1H, J=9 Hz). The mass spectrum showed a molecular ion at m/z 200.

후처리

  1. customdid not rise about 5° C
  2. washwashed with water
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customto give an oily residue
  7. customCrystallization in hexane

출처 및 근거

ORD 기록
ord-78e6d1cf38c14d24b7bae736936f3e0d
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05529583

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