Acetic Acid → 4,4-Dimethyl-3,4-dihydro-2H-naphthalen-1-one

HRID 495898

反応式

HRID 495898 の反応式
[C:1]([OH:4])(=O)[CH3:2].C(OC(=O)C)(=O)C.[CH3:12][C:13]1([CH3:23])[C:22]2[C:17](=[CH:18]C=C[CH:21]=2)[CH2:16][CH2:15][CH2:14]1>C1C=CC=CC=1.O>[CH3:12][C:13]1([CH3:23])[C:14]2[C:2](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:1](=[O:4])[CH2:21][CH2:22]1

参加物

6

反応物 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 161371,1-Dimethyl-1,2,3,4-tetrahydronaphthalene

生成物 1

HCID 2365474,4-Dimethyl-3,4-dihydro-2H-naphthalen-1-one収率 74%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒2 回HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

A solution of 350 ml of glacial acetic acid and 170 ml of acetic anhydride was cooled to 0° C. and CrO3, 25.0 g (0.25 mol) carefully added in small portions. The resulting mixture was stirred for 30 minutes before 120 ml of benzene was added. 1,2,3,4-tetrahydro-1,1-dimethylnaphthalene was added slowly as a solution in 30 ml of benzene. Upon completing the addition the reaction was stirred for 4 hours at 0° C. The solution was diluted with H2O (200 ml) and extracted with Et2O (5×50 ml). The combined organic layers were washed with water, saturated aqueous NaCO3, and saturated aqueous NaCl, before being dried over MgSO4. Removal of the solvents under reduced pressure, and distillation afforded 16.0 g (74%) of the product as a pale-yellow oil, bp 93-96° C./0.3 mm Hg 1H NMR (CDCl13): δ 8.02 (1H, dd, J=1.3, 7.8 Hz), 7.53 (1H, m), 7.42 (1H, d, J=7.9 Hz), 7.29 (1H, m), 2.74 (2H, t, J=6.8 Hz), 2.02 (2H, t, J=6.8 Hz), 1.40 (6H, s).

後処理

  1. additionCrO3, 25.0 g (0.25 mol) carefully added in small portions
  2. additionwas added
  3. additionthe addition the reaction
  4. extractionextracted with Et2O (5×50 ml)
  5. washThe combined organic layers were washed with water, saturated aqueous NaCO3, and saturated aqueous NaCl
  6. dry with materialbefore being dried over MgSO4
  7. customRemoval of the solvents
  8. distillationunder reduced pressure, and distillation

出典と根拠

ORDレコード
ord-8426cfbfe7ce4e30aa317e733e03c29c
出典データセット
uspto-grants-2005_09
特許番号
US06942980B1

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