Carbon Dioxide → HCID 14491966、化合物

HRID 394464

反応式

HRID 394464 の反応式
Cl[CH2:2][C:3]([O-:5])=[O:4].[CH2:6]1O[CH2:7]1.C(Br)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:20](=O)=O>[Pd].C1C=CC=CC=1.C(O)(=O)C>[CH3:20][CH:14]([CH2:13][CH2:12][CH2:11][CH2:10][CH2:6][CH3:7])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:2][C:3]([OH:5])=[O:4]

参加物

8

反応物 4

HCID 280Carbon DioxideHCID 6354Ethylene OxideHCID 81731-BromodecaneHCID 518964Chloroacetate

生成物 1

HCID 14491966HCID 14491966、化合物

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 176Acetic Acid溶媒HCID 241Benzene溶媒

実験手順

See GENERAL PROCEDURE I. Hexyl bromide (compound (1), R═CH3(CH2)5—) is converted to its Grignard reagent with magnesium in dry ether (I, Step (a)). To this is added 5-chloro-2-pentanone (Aldrich C6,2660-3) (I, Step (b)). The reaction mixture is worked up with acetic anhydride (I, Step (c)) to form chloroacetate (3). Acetic acid is eliminated by refluxing (3) in a suitable solvent, e.g., benzene (I, Step (d)) yielding a mixture of chloro-olefin isomers (4) (R═CH3(CH2)5—). (4) is converted to its Grignard reagent following standard practice. (I, Step (e)). The Grignard reagent is treated with ethylene oxide followed by aqueous acidic workup (I, Step (h)), hydrogenation (I, Step (i)), Pd catalyst, and hydrobromination (I, Step (j)). The alkyl bromide (6) (R═CH3(CH2)5—, y=5) is converted to the Grignard reagent with magnesium (1, Step (k)), which is treated with carbon dioxide and aqueous acidic workup (I, Step (1)) to give the product, 7-methyltridecanoic acid, (7).

後処理

  1. customyielding

出典と根拠

ORDレコード
ord-d5f3fee241d74ddbb9e66f54e16b8d89
出典データセット
uspto-grants-2003_08
特許番号
US06602845B2

関連ノート

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