Sodium Hydroxide → HCID 21416427, compound

HRID 442278Notes

Reaction equation

HRID 442278 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[C:5](=[C:7]([CH2:18][CH:19]=[CH2:20])[CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH:10]=1)[OH:6].[OH-].[Na+]>CO>[CH2:18]([C:7]1[C:5]([OH:6])=[C:4]([CH:10]=[C:9]([C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)[CH:8]=1)[C:3]([OH:21])=[O:2])[CH:19]=[CH2:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21416472HCID 21416472, compound

Product 1

HCID 21416427HCID 21416427, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3.9 g. methyl-3-allyl-5-(4'-fluorophenyl)-salicylate, 40 ml. of methanol, and 10 ml. of 2.5 N sodium hydroxide solution is heated at reflux for 15 minutes. The mixture is concentrated in vacuo to remove methanol, diluted to 60 ml. with water, and acidified with dilute hydrochloric acid. The product is collected by filtration, dried, and recrystallized from benzene. The yield of 3-allyl-5-(4'-fluorophenyl)-2-hydroxy-benzoic acid is 3.4 g., m.p. 170° - 172° C.

Workup

  1. additionA mixture of 3.9 g
  2. temperatureat reflux for 15 minutes
  3. concentrationThe mixture is concentrated in vacuo
  4. customto remove methanol
  5. additiondiluted to 60 ml
  6. filtrationThe product is collected by filtration
  7. customdried
  8. customrecrystallized from benzene

Sources & evidence

ORD record
ord-d518fa1d1c6549cb96168e9f1e31b7ec
Source dataset
uspto-grants-1977_08
Patent number
US04044049

Reaction notes

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