Water → 1-Cyclohexene-1-propanal, 4,4-dimethyl-

HRID 585467

反応式

HRID 585467 の反応式
O.[CH3:2][C:3]1([CH3:13])[CH2:8][CH2:7][C:6]([CH2:9][CH2:10][CH2:11][OH:12])=[CH:5][CH2:4]1.[O-]Cl.[Na+]>[Na+].[Br-].CCOC(C)=O>[CH3:2][C:3]1([CH3:13])[CH2:8][CH2:7][C:6]([CH2:9][CH2:10][CH:11]=[O:12])=[CH:5][CH2:4]1

参加物

6

反応物 3

HCID 962WaterHCID 223368773-(4,4-Dimethyl-cyclohex-1-enyl)-propan-1-olHCID 23665760Sodium Hypochlorite

生成物 1

HCID 223368791-Cyclohexene-1-propanal, 4,4-dimethyl-収率 71.8%

試薬・触媒・溶媒 2

HCID 253881Sodium Bromide触媒HCID 8857Ethyl Acetate溶媒

実験手順

PIPO (CAS RN: 091993-31-6; 5.04 g, 0.017 mol), NaBr (0.60 g, 0.006 mol) and KHCO3 (6.40, 0.063 mol) were charged in a 2 1 reactor together with water (60 g), EtOAc (250 g) and 3-(4,4-dimethyl-cyclohex-1-enyl)-propan-1-ol (100.0 g, 0.573 mol, purity: 96.5%). The pot temperature was set to 25° C. and 13% w/w aqueous NaOCl (426.8 g, 0.745 mol) was introduced over 2 hours. Stirring was continued for 1 hour and then the aqueous phase separated. Then 300 g of a 2% w/w aqueous ascorbic acid was added, and the reaction mixture was stirred for 1 hour. The aqueous phase was separated and the organic phase washed with NaHCO3 and then with water. The organic phase thus obtained was concentrated and the crude product purified by a flash distillation (58°–60° C., 1 hPa) to yield 68.4 g of 3-(4,4-dimethyl-1-cyclohexen-1-yl)propanal (yield: 66%; GC purity: 92.3%).

後処理

  1. customwas set to 25° C.
  2. customthe aqueous phase separated
  3. additionThen 300 g of a 2% w/w aqueous ascorbic acid was added
  4. stirringthe reaction mixture was stirred for 1 hour
  5. customThe aqueous phase was separated
  6. washthe organic phase washed with NaHCO3
  7. customThe organic phase thus obtained
  8. concentrationwas concentrated
  9. distillationthe crude product purified by a flash distillation (58°–60° C., 1 hPa)

出典と根拠

ORDレコード
ord-5930c14387804a7aadaa10c2e04f523c
出典データセット
uspto-grants-2005_08
特許番号
US06933265B2

関連ノート

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