tert-Butanol → Ethyl 7-hydroxy-6-tert-butyl-1,4-benzodioxin-2-carboxylate

HRID 1756030Notes

Reaction equation

HRID 1756030 reaction equation
[C:1](O)([CH3:4])([CH3:3])[CH3:2].[OH:6][C:7]1[CH:8]=[CH:9][C:10]2[O:15][CH:14]=[C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[O:12][C:11]=2[CH:21]=1>FC(F)(F)C(O)=O>[OH:6][C:7]1[C:8]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:9][C:10]2[O:15][CH:14]=[C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[O:12][C:11]=2[CH:21]=1

Participants

4

Reactant 2

HCID 6386tert-ButanolHCID 15372688Ethyl 7-hydroxy-1,4-benzodioxin-2-carboxylate

Product 1

HCID 19392459Ethyl 7-hydroxy-6-tert-butyl-1,4-benzodioxin-2-carboxylateYield 78%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Add 0.425 cm3 (4.5 mmol) of tert-butanol to a solution of 0.5 g (2.25 mmol) of ethyl 7-hydroxy-1,4-benzodioxin-2-carboxylate in 3 cm3 of trifluoroacetic acid. The whole is stirred for 24 hours at room temperature and, after concentrating to dryness under reduced pressure, the crude product is then purified by chromatography on a silica column (eluant: petroleum ether/diethyl ether 80:20). Ethyl 7-hydroxy-6-tert-butyl-1,4-benzodioxin-2-carboxylate is obtained in a yield of 78%. Melting point: 222° C. ##STR44##

Workup

  1. concentrationafter concentrating to dryness under reduced pressure
  2. customthe crude product is then purified by chromatography on a silica column (eluant: petroleum ether/diethyl ether 80:20)

Sources & evidence

ORD record
ord-4ea3721ea42847aa89770cff14711be2
Source dataset
uspto-grants-1995_08
Patent number
US05439909

Reaction notes

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