Water → 1-Benzylcyclobutane-1-carboxylic acid

HRID 728696Notes

Reaction equation

HRID 728696 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+].O>C(O)C>[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 3

HCID 962Water2×HCID 14798Sodium HydroxideHCID 15632049Ethyl 1-benzylcyclobutane-1-carboxylate

Product 1

HCID 156705181-Benzylcyclobutane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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-6372054f83d24c2b88224dd64c05a094
Source dataset
uspto-grants-1991_09
Patent number
US05049696

Reaction notes

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