Isobutylene oxide → 2-[1-(3,3-Dimethyl-cyclohexyl)-ethoxy]-2-methyl-propan-1-ol

HRID 132980

反応式

HRID 132980 の反応式
[Cl-].[Cl-].C([Al+2])C.[CH3:6][C:7]1([CH3:16])[CH2:12][CH2:11][CH2:10][CH:9]([CH:13]([OH:15])[CH3:14])[CH2:8]1.[CH3:17][C:18]1([O:21][CH2:20]1)[CH3:19]>C1(C)C=CC=CC=1.C1CCCCC1>[CH3:16][C:7]1([CH3:6])[CH2:12][CH2:11][CH2:10][CH:9]([CH:13]([O:15][C:18]([CH3:19])([CH3:17])[CH2:20][OH:21])[CH3:14])[CH2:8]1

参加物

6

反応物 3

HCID 11208Isobutylene oxideHCID 91338Cyclohexanemethanol, alpha,3,3-trimethyl-HCID 16686341Ethyl aluminium dichloride

生成物 1

HCID 120220122-[1-(3,3-Dimethyl-cyclohexyl)-ethoxy]-2-methyl-propan-1-ol収率 38%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8078Cyclohexane溶媒

実験手順

At 0° C. under an atmosphere of nitrogen, 178 ml (321 mmol) of a 1.8 M solution of ethyl aluminium dichloride in toluene was slowly added to a stirred solution of 100 g (641 mmol) of 1-(3′,3′-dimethylcyclohexyl)ethanol and 55.4 g (769 mmol) of isobutylenoxide in 500 ml of cyclohexane. After complete addition, the cooling bath was removed, the reaction mixture was allowed to warm to room temperature, and stirring was continued at this temperature for 15 h. The reaction mixture was then poured into 1 L of brine, acidified with concentrated phosphoric acid, and thrice extracted with ether. The combined organic extracts were washed with brine and water, dried with sodium sulphate, and concentrated on a rotary evaporator. Distillation of the crude material (136 g) provided at 78-85° C./0.3 mbar 55.1 g (38%) of pure 2-[1′-(3″,3″-dimethylcyclohexyl)-ethoxy]-2-methylpropan-1-ol, while 60.4 g of starting material were recovered.

後処理

  1. additionAfter complete addition
  2. customthe cooling bath was removed
  3. additionThe reaction mixture was then poured into 1 L of brine
  4. extractionextracted with ether
  5. washThe combined organic extracts were washed with brine and water
  6. dry with materialdried with sodium sulphate
  7. concentrationconcentrated on a rotary evaporator
  8. distillationDistillation of the crude material (136 g)

出典と根拠

ORDレコード
ord-c2a06d032eff4e9d975790186acbc953
出典データセット
uspto-grants-2008_06
特許番号
US07390779B2

関連ノート

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