Sodium Hydroxide → 2-Phenylhexahydro-2,5-methanopentalene-3a-carboxylic acid

HRID 2405744ノート

反応式

HRID 2405744 の反応式
[OH-].[Na+].BrBr.[C:5]1([C:11]23[CH2:22][CH:15]4[CH2:16][C:17]([C:19](=[O:21])C)([CH2:18]2)[CH:13]([CH2:14]4)[CH2:12]3)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C[O:24]C(C)(C)C>O.O1CCOCC1>[C:5]1([C:11]23[CH2:22][CH:15]4[CH2:16][C:17]([C:19]([OH:24])=[O:21])([CH2:18]2)[CH:13]([CH2:14]4)[CH2:12]3)[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 15413tert-Butyl methyl etherHCID 24408BromineHCID 593749561-(2-Phenylhexahydro-2,5-methanopentalen-3a-yl)ethanone

生成物 1

HCID 673007182-Phenylhexahydro-2,5-methanopentalene-3a-carboxylic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 312751,4-Dioxane溶媒2 回

実験手順

Dioxane (1.81) was added to a solution, cooled to −22° C., of sodium hydroxide (724 g) in water (4.8 l). Bromine (578 g) was metered into this solution such that a temperature of −15° C. was not exceeded. A solution of 1-(2-phenylhexahydro-2,5-methanopentalen-3a-yl)ethanone (290 g) in dioxane (600 ml) was metered into this solution, and the reaction was allowed to warm up gradually to room temperature. tert-Butyl methyl ether was added. Subsequently, water was metered in (2.5 l). After phase separation, the aqueous phase was washed with tert-butyl methyl ether. Subsequently, after addition of tert-butyl methyl ether (5 l), hydrochloric acid (32%) was used to establish a pH of pH 1.5. After phase separation, the organic phase was washed repeatedly with water and clarified with activated carbon. The solvent was changed by distillation under reduced pressure with addition of diisopropyl ether. After extractive stirring with diisopropyl ether at reflux, 2-phenylhexahydro-2,5-methanopentalene-3a-carboxylic acid (292 g) was obtained as a solid with 95% purity.

後処理

  1. customwas metered into this solution such that a temperature of −15° C.
  2. customAfter phase separation
  3. washthe aqueous phase was washed with tert-butyl methyl ether
  4. additionSubsequently, after addition of tert-butyl methyl ether (5 l), hydrochloric acid (32%)
  5. customAfter phase separation
  6. washthe organic phase was washed repeatedly with water
  7. distillationThe solvent was changed by distillation under reduced pressure with addition of diisopropyl ether
  8. temperatureat reflux

出典と根拠

ORDレコード
ord-a5b4370320d840ac8341b02b74f56aef
出典データセット
uspto-grants-2014_08
特許番号
US08809325B2

反応ノート

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