Methyl 4-Formylbenzoate → HCID 13833722, compound

HRID 1382901Notes

Reaction equation

HRID 1382901 reaction equation
[Br-].[CH3:2][C:3]1([CH3:34])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH:13]([P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH3:14])[CH:11]=2)[O:6][CH2:5][CH2:4]1.[CH:35]([C:37]1[CH:46]=[CH:45][C:40]([C:41]([O:43][CH3:44])=[O:42])=[CH:39][CH:38]=1)=O>O1C(CC)C1>[CH3:34][C:3]1([CH3:2])[C:12]2[C:7](=[CH:8][CH:9]=[C:10](/[C:13](/[CH3:14])=[CH:35]/[C:37]3[CH:46]=[CH:45][C:40]([C:41]([O:43][CH3:44])=[O:42])=[CH:39][CH:38]=3)[CH:11]=2)[O:6][CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 15294Methyl 4-FormylbenzoateHCID 199355281-(4,4-Dimethyl-6-chromanyl)ethyltriphenylphosphonium bromide

Product 1

HCID 13833722HCID 13833722, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 78341,2-EpoxybutaneSolvent

Procedure

A solution of 2.0 g (3.8 mmol) of 1-(4,4-dimethyl-6-chromanyl)ethyltriphenylphosphonium bromide and 630 mg (3.8 mmol) of methyl 4-formylbenzoate in 100 ml of 1,2-epoxybutane was heated under reflux for 72 hours. The reaction mixture was then concentrated in vacuo to an oil. The oil was purified by column chromatography on silicic acid, eluting with ether-hexane (1:9). This afforded mg (27% yield) of the title compound as a solid, mp 92°-95° C.

Workup

  1. temperatureunder reflux for 72 hours
  2. concentrationThe reaction mixture was then concentrated in vacuo to an oil
  3. customThe oil was purified by column chromatography on silicic acid
  4. washeluting with ether-hexane (1:9)

Sources & evidence

ORD record
ord-08edafbf10a046bea055a7d51fd83fa5
Source dataset
uspto-grants-1989_02
Patent number
US04808597

Reaction notes

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