tert-Butanol → 4-((tetrahydro-2H-pyran-2-yloxy)methyl)benzyl acetate

HRID 1039798Notes

Reaction equation

HRID 1039798 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][CH:10]=1.[C:17]([OH:21])(C)(C)[CH3:18].C(OC(C)C)(C)C>[Zn]>[C:17]([O:16][CH2:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)=[CH:14][CH:13]=1)(=[O:21])[CH3:18]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 7914Diisopropyl EtherHCID 67139706(4-{[(Oxan-2-yl)oxy]methyl}phenyl)methanol

Product 1

HCID 680079574-((tetrahydro-2H-pyran-2-yloxy)methyl)benzyl acetateYield 92.9%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

Under a nitrogen atmosphere, a mixture of (4-((tetrahydro-2H-pyran-2-yloxy)methyl)phenyl)methanol (3.0 mmol), t-butanol (3.6 mmol), the zinc cluster obtained in the above-described Example 5 (0.0375 mmol), and diisopropyl ether (5.0 ml) was refluxed for 18 hours. As a result, 4-((tetrahydro-2H-pyran-2-yloxy)methyl)benzyl acetate was obtained in a yield of 92.9%.

Workup

  1. temperaturewas refluxed for 18 hours

Sources & evidence

ORD record
ord-a827e590f89b49bfa3be32e99c973f13
Source dataset
uspto-grants-2013_10
Patent number
US08552204B2

Reaction notes

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