1-Methoxy-2-propanol → (2-Methoxy-1-methylethoxy)acetic Acid Ethyl Ester

HRID 18831

Reaction equation

HRID 18831 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([OH:6])[CH3:5].[N+](=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N-]>ClCCl.CCCCCCC.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:13]([O:12][C:10](=[O:11])[CH2:9][O:6][CH:4]([CH3:5])[CH2:3][O:2][CH3:1])[CH3:14]

Participants

6

Reactant 2

HCID 79001-Methoxy-2-propanolHCID 12192Ethyl diazoacetate

Product 1

HCID 64044950(2-Methoxy-1-methylethoxy)acetic Acid Ethyl EsterYield 64.9%

Reagents, catalysts & solvents 3

HCID 423677Acetic acid, rhodium salt (4:2)CatalystHCID 6344DichloromethaneSolventHCID 8900HeptaneSolvent

Procedure

To a solution of 1-methoxy-2-propanol (900 mg, 10.0 mmol) in dichloromethane (20 mL) is added rhodium (II) acetate dimer (10 mg) followed by ethyl diazoacetate (0.95 mL, 9.0 mmol). The reaction mixture is stirred at rt for 30 min. The reaction mixture is diluted with heptane, filtered through Celite, and the filtrate is evaporated and the residue is vacuum distilled at 133° C. to give 1.03 g of the product 473. 1H NMR (CDCl3) δ 4.20 (q, 2H), 3.72 (m, 1H), 3.45 (dd, 1H), 3.37 (dd, 1H), 3.35 (s, 3H), 1.27 (t, 3H), 1.19 (d, 3H).

Workup

  1. filtrationfiltered through Celite
  2. customthe filtrate is evaporated
  3. distillationdistilled at 133° C.

Sources & evidence

ORD record
ord-6478a7aef5894c6b944da9c656f93df6
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Linked notes

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