monoMethyl adipate → 6-(4-Hexylphenyl)-6-oxohexanoic acid

HRID 1720140Notes

Reaction equation

HRID 1720140 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:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].[Cl-].[Al+3].[Cl-].[Cl-].[OH-].[Na+]>C(O)C>[CH2:16]([C:22]1[CH:23]=[CH:24][C:25]([C:3]([CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[O:11])=[CH:26][CH:27]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

7

Reactant 5

HCID 12328monoMethyl adipateHCID 14109HexylbenzeneHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 152955616-(4-Hexylphenyl)-6-oxohexanoic acidYield 25%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Adipic acid monomethyl ester (50 g; 0.31 mole) is converted to the acid chloride with thionyl chloride (50 g) by the manner described in Example 1. This product is reacted with hexylbenzene (100 g) and aluminum chloride (62.4 g; 0.47 mole) and the product isolated in a manner analogous to that described in Example 1. The crude product is heated under reflux in ethanol (234 ml) and 2N sodium hydroxide (234 ml) for 4 hours. The reaction mixture is then processed as described in Example 1. The product is recrystallized from aqueous ethanol to give 5-(4-n-hexylbenzoyl)pentanoic acid as colorless crystals (22.5 g), m.p. 77°-79° C.

Workup

  1. customthe product isolated in a manner analogous to
  2. customThe product is recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-45ff4f8574a14e859b3f8fa99c9e2dc8
Source dataset
uspto-grants-1996_04
Patent number
US05504244

Reaction notes

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