tert-Butanol → HCID 53838810, compound

HRID 1765445Notes

Reaction equation

HRID 1765445 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[C:4]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:3]=1.C(Cl)(=O)C(Cl)=O.[C:26](O)([CH3:29])([CH3:28])[CH3:27]>C1(C)C=CC=CC=1>[C:26]([O:10][C:9](=[O:11])[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][C:4]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:29])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 65578Oxalyl chlorideHCID 14519886HCID 14519886, compound

Product 1

HCID 53838810HCID 53838810, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneCatalyst

Procedure

To a solution of [4-methyl-2-(phenylmethoxy)phenyl]acetic acid (10.25 g, 40 mmol) in toluene (70 ml containing 2 drops of DMF) was added oxalyl chloride (4.0 ml, 46 mmol, 1.15 equivalents) dropwise, the mixture was stirred at room temperature for 5 hr then 44 ml of tert-butanol was added, the resulting solution was stirred at room temperature for 20 hr. The solvents were evaporated and the residue obtained was purified by chromatography on silica gel (EtOAc-hexanes, 1:40 to 1:25) to provide the desired product [4-methyl-2-(phenylmethoxy)-phenyl]acetic acid tert-butyl ester as an oil (11.70 g, 92.8% yield). 1H NMR (CDCl3) δ: 7.521˜7.364 (5H, m), 7.147 (1H, d, J=7.81 Hz), 6.810 (2H, m), 5.118 (2H, s), 3.629 (2H, S), 2.391 (3H, s), 1.461 (9H, s) ppm.

Workup

  1. stirringthe resulting solution was stirred at room temperature for 20 hr
  2. customThe solvents were evaporated
  3. customthe residue obtained
  4. customwas purified by chromatography on silica gel (EtOAc-hexanes, 1:40 to 1:25)

Sources & evidence

ORD record
ord-f12aeefb928b4425ae8a995897f0c983
Source dataset
uspto-grants-2007_06
Patent number
US07226991B1

Reaction notes

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