Sodium Hydroxide → 1-Benzylcyclobutane-1-carboxylic acid

HRID 231608Notes

Reaction equation

HRID 231608 reaction equation
[C:1]1([CH2:7][C:8]2([C:12]([O:14]CC)=[O:13])[CH2:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C.O>[C:1]1([CH2:7][C:8]2([C:12]([OH:14])=[O:13])[CH2:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 15632049Ethyl 1-benzylcyclobutane-1-carboxylate

Product 1

HCID 156705181-Benzylcyclobutane-1-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of ethyl 1-phenylmethylcyclobutanecarboxylate (4.16 g, 19.1 mmol), sodium hydroxide (1.2 g, 30 mmol) in ethanol (95%, 20 ml) and water (5 ml) was stirred at room temperature for 60 hours. The reaction mixture was poured into cold water and extracted with diethyl ether. The aqueous phase was separated, acidified with HCl (2N, 35 ml) and extracted with diethyl ether. The latter extract was washed with water, dried, filtered and evaporated to afford the desired product as a pale yellow oil: NMR (CDCl3) δ=1.7~2.6 (6H, m), 3.10 (2H, s), 7.22 (5H, s).

Workup

  1. extractionextracted with diethyl ether
  2. customThe aqueous phase was separated
  3. extractionextracted with diethyl ether
  4. extractionThe latter extract
  5. washwas washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-e4e4564fde5e436f815be29d73e6aca3
Source dataset
uspto-grants-1989_07
Patent number
US04847306

Reaction notes

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