monoMethyl adipate → HCID 15295562, compound

HRID 1720141Notes

Reaction equation

HRID 1720141 reaction equation
CO[C:3](=[O:11])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9].S(Cl)(Cl)=O.[CH2:16]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[Cl-].[Al+3].[Cl-].[Cl-].[OH-].[Na+]>C(O)C>[CH2:16]([C:24]1[CH:25]=[CH:26][C:27]([C:3]([CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[O:11])=[CH:28][CH:29]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

7

Reactant 5

HCID 12328monoMethyl adipateHCID 14798Sodium HydroxideHCID 16607OctylbenzeneHCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 15295562HCID 15295562, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Adipic acid monomethyl ester (25 g; 0.16 mole) is converted to the acid chloride with thionyl chloride (25 g) in a manner analogous to that described in Example 1. The crude product is reacted with octylbenzene (200 ml) and aluminum chloride (40 g; 0.3 mole) and the product isolated in a manner analogous to that described in Example 1. The crude product Is heated under reflux with 2N sodium hydroxide (117 ml) and ethanol (117 ml) for 2 hours and further processed as described in Example 1. The crude product is recrystallized from heptane to give 5-(4-n-octylbenzoyl)pentanoic acid (38.2 g), m.p. 96°-97° C.

Workup

  1. customthe product isolated in a manner analogous to
  2. customThe crude product is recrystallized from heptane

Sources & evidence

ORD record
ord-a5dfe91139f7497e8ba5b71a0cbe3543
Source dataset
uspto-grants-1996_04
Patent number
US05504244

Reaction notes

Loading…