Carbon Dioxide → HCID 14491966, compound

HRID 394464

Reaction equation

HRID 394464 reaction equation
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]

Participants

8

Reactant 4

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

Product 1

HCID 14491966HCID 14491966, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 241BenzeneSolvent

Procedure

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).

Workup

  1. customyielding

Sources & evidence

ORD record
ord-d5f3fee241d74ddbb9e66f54e16b8d89
Source dataset
uspto-grants-2003_08
Patent number
US06602845B2

Linked notes

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