Butanoic acid, 2-bromo-, ethyl ester → HCID 20365471, compound

HRID 1678975Notes

Reaction equation

HRID 1678975 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[Na].Br[CH:16]([CH2:22][CH3:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18]>C(O)C>[O:11]1[CH2:10][CH2:9][CH:8]([C:5]2[CH:6]=[CH:7][C:2]([O:1][CH:16]([CH2:22][CH3:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:3][CH:4]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 79039Butanoic acid, 2-bromo-, ethyl esterHCID 5360545SodiumHCID 227373584-(Oxan-4-yl)phenol

Product 1

HCID 20365471HCID 20365471, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 44.6 g of 4-(p-hydroxyphenyl)-tetrahydropyran in 50 ml of ethanol was added at 20° C to a mixture of 5.75 g of sodium in 250 ml of ethanol and the mixture was stirred for one hour and then was cooled to 0° C. 55.1 ml of ethyl 2-bromo-butyrate were added to the reaction mixture which was then allowed to return to 20° C and was refluxed overnight. The ethanol was evaporated and the residue was taken up in 50 ml of 1N sodium hydroxide and 250 ml of methylene chloride. The aqueous phase was decanted and was extracted again with methylene chloride. The organic phases were dried and evaporated to dryness to obtain 56.3 g of raw product which was rectified under reduced pressure to obtain 40 g of ethyl 2-[p-(4-tetrahydropyranyl)-phenoxy]-butanoate with a boiling point of 143° C. at 0.3 mm Hg.

Workup

  1. customto return to 20° C
  2. temperaturewas refluxed overnight
  3. customThe ethanol was evaporated
  4. customThe aqueous phase was decanted
  5. extractionwas extracted again with methylene chloride
  6. customThe organic phases were dried
  7. customevaporated to dryness
  8. customto obtain 56.3 g of raw product which

Sources & evidence

ORD record
ord-1e5b3bbf58d44a4fb8cb872fdb5fda7d
Source dataset
uspto-grants-1978_03
Patent number
US04078076

Reaction notes

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