Hydrochloric Acid → Methyl 2-(4-isobutyrylphenoxy)acetate

HRID 646215

Reaction equation

HRID 646215 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5](Cl)(=[O:9])[CH:6]([CH3:8])[CH3:7].[CH3:11][O:12][C:13]([CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].Cl>CCCCCC.C(OCC)(=O)C>[C:5]([C:20]1[CH:21]=[CH:22][C:17]([O:16][CH2:15][C:13]([O:12][CH3:11])=[O:14])=[CH:18][CH:19]=1)(=[O:9])[CH:6]([CH3:8])[CH3:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 16365Methyl phenoxyacetateHCID 62325Isobutyryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 12797090Methyl 2-(4-isobutyrylphenoxy)acetate

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To an oven-dried round bottom flask was added anhydrous AlCl3 (24.1 g, 0.18 mol), which was subsequently purged with Ar. Methylene chloride (10 mL) was added via syringe and the resulting slurry was cooled to 0° C. in an ice bath. The isobutryl chloride (6.9 mL, 6.6×10−2 mol) was added dropwise via syringe. The methyl phenoxy acetate (8.7 mL, 6.0×10−2 mol) was added dropwise via syringe. The reaction was stirred until deemed complete by thin layer chromatography (TLC) (25% ethyl acetate in hexane) (approximately 2 h). The reaction mixture was poured slowly into a mixture of ice (100 g) and concentrated HCl (40 mL). The organic layer was separated and the organic layer extracted with methylene chloride (3×100 mL). The combined organic layers were washed with water (3×100 mL) and dried over MgSO4. The solvent was removed in vacuo to reveal 14 g of a white, crystalline solid (quantitative yield). 1H NMR (300 NMR, CDCl3) δ7.97 (2H, d, J=8.9 Hz), 6.96 (2H, J=8.9 Hz), 4.71 (2H, s), 3.82 (3H, s), 3.51 (1H, septet, J=6.8 Hz), 1.22 (6H, d, J=6.8 Hz).

Workup

  1. customwas subsequently purged with Ar
  2. additionMethylene chloride (10 mL) was added via syringe
  3. customThe organic layer was separated
  4. extractionthe organic layer extracted with methylene chloride (3×100 mL)
  5. washThe combined organic layers were washed with water (3×100 mL)
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-046a7f7af1ad4bf9b8aaee2407ce74b2
Source dataset
uspto-grants-2010_04
Patent number
US07705065B2

Linked notes

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