Pyridine → 2-Phenylbutyric Acid

HRID 1722479Notes

Reaction equation

HRID 1722479 reaction equation
[C:1]1([CH:7]([CH2:22][CH3:23])[C:8]([O:10]C(=O)C(C2C=CC=CC=2)CC)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1>C(OCC)C>[C:1]1([CH:7]([CH2:22][CH3:23])[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 1049PyridineHCID 1026412-Phenylbutanoic anhydride

Product 1

HCID 70122-Phenylbutyric AcidYield 91.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 2,3-isopropylidene-D(+)-ribono-1,4-lactone (188 mg) and 2-phenylbutyric anhydride (310 mg) in d5 -pyridine (0.35 ml) was monitored by 1H n.m.r. until reaction was complete (1.5 hours). The mixture was dissolved in diethyl ether (20 ml), partitioned with aqueous hydrochloric acid (2×20 ml, 1M) and aqueous sodium hydroxide (2×10 ml, 1M). The combined alkaline extracts were acidified with 10M hydrochloric acid to pH 2, extracted with diethyl ether (2×10 ml) and the dried (MgSO4) ether extracts concentrated in vacuo to give (+)2-phenylbutyric acid (150 mg), [α]D25 +31° (c=1.0, benzene).

Workup

  1. customuntil reaction
  2. custom(1.5 hours)
  3. custompartitioned with aqueous hydrochloric acid (2×20 ml, 1M) and aqueous sodium hydroxide (2×10 ml, 1M)
  4. extractionextracted with diethyl ether (2×10 ml)
  5. dry with materialthe dried (MgSO4) ether
  6. concentrationextracts concentrated in vacuo

Sources & evidence

ORD record
ord-b09d73dd90b1441280a14f4bc85c7963
Source dataset
uspto-grants-1989_08
Patent number
US04855446

Reaction notes

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