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4-[4-(1-Adamantyl)-phenoxy]-2-butenoic acid → 4-[4-(1-Adamantyl)-phenoxy]butyric acid

HRID 258984
Notes
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Reaction equation

HRID 258984 reaction equation
[C:1]12([C:11]3[CH:23]=[CH:22][C:14]([O:15][CH2:16][CH:17]=[CH:18][C:19]([OH:21])=[O:20])=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C12(C3C=CC(OC=CCC(O)=O)=CC=3)CC3CC(CC(C3)C1)C2.[H][H]>[Pd].CO>[C:1]12([C:11]3[CH:12]=[CH:13][C:14]([O:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:22][CH:23]=3)[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 544821354-[4-(1-Adamantyl)-phenoxy]-2-butenoic acidHCID 545391144-[4-(1-Adamantyl)-phenoxy]-3-butenoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 214251534-[4-(1-Adamantyl)-phenoxy]butyric acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst
HCID 887
Methanol
Solvent

Procedure

A solution of 0.9 g of the mixture of 4-[4-(1-adamantyl)-phenoxy]-2-butenoic acid and 4-[4-(1-adamantyl)-phenoxy]-3-butenoic acid is 30 ml of absolute methanol is hydrogenated with 0.3 g of palladium (5% strength on charcoal) until 1 equivalent of hydrogen has been taken up (normal pressure, about 25° C). The catalyst is then filtered off, and the filtrate is mixed with 10 ml of 2 N sodium hydroxide solution and left to stand for 24 hours at about 25° C. It is then evaporated in vacuo to half its volume. The evaporation residue is partitioned between 50 ml of 2 N hydrochloric acid and 3 times 50 ml of methylene chloride. The organic phases are washed until neutral, dried over sodium sulphate and evaporated in vacuo. Crystallisation of the evaporation residue from ethanol gives 4-[4-(1-adamantyl)-phenoxy]butyric acid of melting point 170°-172° C.

Workup

  1. custom(normal pressure, about 25° C)
  2. filtrationThe catalyst is then filtered off
  3. additionthe filtrate is mixed with 10 ml of 2 N sodium hydroxide solution
  4. waitleft
  5. customIt is then evaporated in vacuo to half its volume
  6. customThe evaporation residue is partitioned between 50 ml of 2 N hydrochloric acid and 3 times 50 ml of methylene chloride
  7. washThe organic phases are washed until neutral,
  8. dry with materialdried over sodium sulphate
  9. customevaporated in vacuo
  10. customCrystallisation of the evaporation residue from ethanol

Sources & evidence

ORD record
ord-c5b93fae33c14131815bb0db3b43ad8c
Source dataset
uspto-grants-1977_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04035413

Reaction notes

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