Formaldehyde → 6-Benzyloxy-3-methylene-4-chromanone

HRID 1276312Notes

Reaction equation

HRID 1276312 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][CH2:14][CH2:13][C:12]2=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:21]NC.C=O>C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][CH2:14][C:13](=[CH2:21])[C:12]2=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 144227766-(Benzyloxy)chroman-4-one

Product 1

HCID 144227906-Benzyloxy-3-methylene-4-chromanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 9.2 g of 6-benzyloxy-4-chromanone, dimethylamine hydrochloride and 1.3 g of paraformaldehyde in 100 ml of acetic acid was heated on a steam bath for 5 hours. The volatiles were evaporated in vacuo and the residue was purified on silica gel, eluting with CH2Cl2, to give 3.7 g of product, Rf (CH2Cl2)=0.5.

Workup

  1. customThe volatiles were evaporated in vacuo
  2. customthe residue was purified on silica gel
  3. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-987da6e8538a495581d20a1e7063812c
Source dataset
uspto-grants-2000_12
Patent number
US06166031

Reaction notes

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