tert-Butanol → HCID 53661733, compound

HRID 1780036Notes

Reaction equation

HRID 1780036 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10](Cl)=[O:11])[CH:6]=[CH:7][CH:8]=1.[C:13]([OH:17])([CH3:16])([CH3:15])[CH3:14].C(N(CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 27332463-Methoxyphenylacetyl chloride

Product 1

HCID 53661733HCID 53661733, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-methoxyphenyl)acetylchloride (25 g, 135 mmol), in dry dichloromethane (50 ml) was added t-butanol (14 ml) slowly with stirring. After stirring at room temperature for 5 minutes, the reaction was cooled in ice, and triethylamine (20 ml) added dropwise. After stirring a further 2 hours at room temperature, the reaction was poured into saturated aqueous sodium carbonate solution, extracted with dichloromethane, dried (MgSO4), solvents evaporated, and the residue chromatographed on silica (eluted 10% diethyl ether-petroleum ether bp 60°-80°), to give t-butyl (3-methoxyphenyl)acetate. 1H NMR (250 MHz, CDCl3) δ1.38 (9H, s), 3.42 (2H, s), 3.73 (3H, s), 6.69-6.82 (3H, m), 7.17 (1H, t, J=8.4Hz).

Workup

  1. stirringAfter stirring at room temperature for 5 minutes
  2. temperaturethe reaction was cooled in ice
  3. stirringAfter stirring a further 2 hours at room temperature
  4. extractionextracted with dichloromethane
  5. dry with materialdried (MgSO4), solvents
  6. customevaporated
  7. customthe residue chromatographed on silica (eluted 10% diethyl ether-petroleum ether bp 60°-80°)

Sources & evidence

ORD record
ord-72af3a378d6a470d838f7ce8ad1f83cc
Source dataset
uspto-grants-1997_05
Patent number
US05629347

Reaction notes

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