Sodium Hydroxide → HCID 20365473, compound

HRID 1678976Notes

Reaction equation

HRID 1678976 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:21]=[CH:20][C:10]([O:11][CH:12]([CH2:18][CH3:19])[C:13]([O:15]CC)=[O:14])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[O:1]1[CH2:2][CH2:3][CH:4]([C:7]2[CH:8]=[CH:9][C:10]([O:11][CH:12]([CH2:18][CH3:19])[C:13]([OH:15])=[O:14])=[CH:20][CH:21]=2)[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20365471HCID 20365471, compound

Product 1

HCID 20365473HCID 20365473, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 14.6 g of ethyl 2-[p-(4-tetrahydropyranyl)-phenoxy]-butanoate, 100 ml of ethanol and 40 ml of 2N sodium hydroxide was stirred at 20° C for 24 hours and then refluxed for an hour. The ethanol was evaporated and the residue was taken up in 100 ml of 0.5N sodium hydroxide. The solution was washed with ether and acidified with concentrated hydrochloric acid and was extracted with methylene chloride. The extracts were dried and evaporated to dryness to obtain 13.2 g of raw product which was crystallized from cyclohexane to obtain 12.2 g of 2-[p-(4-tetrahydropyranyl)-phenoxy]-butanoic acid melting at 127° C.

Workup

  1. temperaturerefluxed for an hour
  2. customThe ethanol was evaporated
  3. washThe solution was washed with ether
  4. extractionwas extracted with methylene chloride
  5. customThe extracts were dried
  6. customevaporated to dryness
  7. customto obtain 13.2 g of raw product which
  8. customwas crystallized from cyclohexane

Sources & evidence

ORD record
ord-1ad6cc5b47f5473e99ea0dc5003ccfe7
Source dataset
uspto-grants-1978_03
Patent number
US04078076

Reaction notes

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