Hydroquinone → Butyl 6-ethoxy-3-methyl-3,6-dihydro-2H-pyran-2-carboxylate

HRID 28084Notes

Reaction equation

HRID 28084 reaction equation
[CH2:1]([O:3][CH:4]=[CH:5][CH:6]=[CH:7][CH3:8])[CH3:2].[C:9]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])(=[O:12])[CH:10]=[O:11].C1(C=CC(O)=CC=1)O>C(Cl)Cl>[CH2:14]([O:13][C:9]([CH:10]1[CH:7]([CH3:8])[CH:6]=[CH:5][CH:4]([O:3][CH2:1][CH3:2])[O:11]1)=[O:12])[CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 80521Butyl oxoacetate2×HCID 537696421-Ethoxy-1,3-pentadiene2×

Product 1

HCID 23338794Butyl 6-ethoxy-3-methyl-3,6-dihydro-2H-pyran-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure of Example 12, a solution of 26.7 g. (0.226 mol) of 1-ethoxy-1,3-pentadiene (purity, 95%), 32.5 g. (0.25 mol) of butyl glyoxylate and 0.250 g. of hydroquinone in 250 ml. of methylene chloride was refluxed for 48 hours to give 28.0 g. of a mixture of 1-ethoxy-1,3-pentadiene and butyl glyoxylate and 20.32 g. of distilled 2H-pyran butyl ester (b1.0 =100°-110°) as an oil. Yield based on 1-ethoxy-1,3-pentadiene, 34%.

Workup

  1. customto give 28.0 g
  2. customYield

Sources & evidence

ORD record
ord-0c5158962e0540d9b37ae10542502089
Source dataset
uspto-grants-1980_09
Patent number
US04225514

Reaction notes

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