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

HRID 37160Notes

Reaction equation

HRID 37160 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%.

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-3e08b996c1ac45b09fb421f221ec96c7
Source dataset
uspto-grants-1995_05
Patent number
US05420132

Reaction notes

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