Ethanol → 3-[4-(Benzyloxy)phenyl]pentanedioic acid

HRID 1955649Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O:23]CC)(=[O:22])[CH2:18]C(C)=O.N1CCCCC1.C[O-:33].[Na+].[CH2:35]([OH:37])[CH3:36]>>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]([CH2:18][C:17]([OH:23])=[O:22])[CH2:36][C:35]([OH:33])=[O:37])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 5

HCID 702Ethanol

HCID 8082Piperidine

HCID 8868Ethyl Acetoacetate

HCID 78109Benzaldehyde, 4-(phenylmethoxy)-

HCID 10942334Sodium Methoxide

Product 1

HCID 272815823-[4-(Benzyloxy)phenyl]pentanedioic acid

Procedure

4-Benzyloxybenzaldehyde (50.0 g, Aldrich), ethyl acetoacetate (61.31 g, Aldrich), and piperidine (4.01 lg) were reacted together overnight. The resulting mixture was refluxed for 3-4 hours with ethanol (400 ml) and sodium methoxide (63.63 g).

Sources & evidence

ORD record: ord-93fbbd748e0546a3adc53c6cc49e7f46
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05776951

Reaction notes

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