1,2-Epoxybutane → Ethyl 4-(2-hydroxybutoxy)benzoate

HRID 328150Notes

Reaction equation

HRID 328150 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH2:13]1[O:17][CH:14]1[CH2:15][CH3:16].[OH-].[Na+]>>[CH2:9]([O:8][C:6]([C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:13][CH:14]([OH:17])[CH2:15][CH3:16])=[CH:12][CH:11]=1)=[O:7])[CH3:10]

Participants

4

Reactant 3

HCID 78341,2-EpoxybutaneHCID 8434EthylparabenHCID 14798Sodium Hydroxide

Product 1

HCID 21444117Ethyl 4-(2-hydroxybutoxy)benzoateYield 82.4%

Procedure

In a closed vessel 16.7g of ethyl p-hydroxybenzoate, 7.2 g of 1,2-butylene oxide and 0.8 ml of a 50% aqueous solution of sodium hydroxide were heated at 150° C for 4 hours in the same manner as in Example 1. The reaction mixture obtained was treated in the same way as in Example 1 to afford 19.6g of 1-(p-ethoxycarbonylphenoxy)-butan-2-ol (compound No. 48) in an 82% yield, which had a melting point of 52° to 52.5° C when recrystallized from ethyl acetate and n-hexane.

Workup

  1. customThe reaction mixture obtained
  2. additionwas treated in the same way as in Example 1

Sources & evidence

ORD record
ord-17268434114446ba83925a0d128b93ae
Source dataset
uspto-grants-1977_04
Patent number
US04016186

Reaction notes

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