Hydrochloric Acid → HCID 10727374, compound

HRID 1742495Notes

Reaction equation

HRID 1742495 reaction equation
[OH-].[Na+].[Cl-].[CH3:4][O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([O:16][CH3:17])=[CH:8][C:7]=1[CH2:18][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:38]=O.Cl>>[CH3:4][O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([O:16][CH3:17])=[CH:8][C:7]=1[CH:18]=[CH2:38]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 19009237HCID 19009237, compound

Product 1

HCID 10727374HCID 10727374, compound

Procedure

50 ml of a 10% aqueous solution of sodium hydroxide were added dropwise, with stirring, to a mixture of 7.36 g of 1,4-dimethoxy-2-naphthylmethyltriphenylphosphonium chloride [prepared as described in step (a) above] and 75 ml of a 30% V/v aqueous solution of formaldehyde, and the resulting mixture was stirred for 1 hour. At the end of this time, the reaction mixture was neutralized with 3N aqueous hydrochloric acid, after which it was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 24:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 2.45 g of the title compound as a pale yellow oil.

Workup

  1. extractionafter which it was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. customthe solvent was removed by distillation under reduced pressure
  4. customThe resulting residue was purified by column chromatography through silica gel
  5. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-e89b9919450d42e7806c6c8d402796e4
Source dataset
uspto-grants-1994_08
Patent number
US05338855

Reaction notes

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