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

HRID 2053622

Reaction equation

HRID 2053622 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-8989f3fb34994c328bd80739944a466c
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Linked notes

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