Heptanoyl chloride → HCID 86761101, compound

HRID 2233543Notes

Reaction equation

HRID 2233543 reaction equation
COC(=O)[CH:4]([CH3:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11].[C:14](Cl)(=[O:21])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[Cl-].[Al+3].[Cl-].[Cl-]>[N+](C1C=CC=CC=1)([O-])=O>[C:14]([C:9]1[CH:8]=[CH:7][C:6]2[O:11][CH:12]=[CH:4][C:5]=2[CH:10]=1)(=[O:21])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 17313Heptanoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 18974067Methyl 2-hydroxy-α-methylbenzeneacetate

Product 1

HCID 86761101HCID 86761101, compoundYield 9.3%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

To a solution of methyl 2-hydroxyphenylacetic acid methyl ester (1000 mg, 6.02 mmol) in nitrobenzene (10 ml) was added heptanoyl chloride (900 mg, 6.02 mmol), followed by aluminium chloride (1.6 g, 12.0 mmol, 2 equiv). The solution was heated to 60 C for 18 h, then cooled on ice before quenching with aqueous hydrochloric acid (1 M, 50 ml). The mixture was extracted with dichloromethane. (3×50 ml) and concentrated. Chromatography on silica gel using ethyl acetate/petroleum spirits (20:80) as eluant gave a semi-solid yellow residue. Recrystallization from dichloromethane/petroleum spirits at −15 C gave the title compound as a pale yellow solid (129 mg). Mp 64-67° C.;

Workup

  1. temperatureThe solution was heated to 60 C for 18 h
  2. temperaturecooled on ice
  3. custombefore quenching with aqueous hydrochloric acid (1 M, 50 ml)
  4. extractionThe mixture was extracted with dichloromethane
  5. concentration(3×50 ml) and concentrated
  6. customgave a semi-solid yellow residue
  7. customRecrystallization from dichloromethane/petroleum spirits at −15 C

Sources & evidence

ORD record
ord-4fc098d8f3bf4bacab96b733c1e86cbf
Source dataset
uspto-grants-2010_05
Patent number
US07709514B2

Reaction notes

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