Water → Ethyl 4-(2-formyl-3-hydroxyphenoxymethyl)benzoate

HRID 485183Notes

Reaction equation

HRID 485183 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11]OC)[C:3]=1[CH:4]=[O:5].CC(C)([O-])C.[K+].BrC[C:22]1[CH:32]=[CH:31][C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:24][CH:23]=1.O>CS(C)=O>[CH:4]([C:3]1[C:2]([OH:1])=[CH:9][CH:8]=[CH:7][C:6]=1[O:10][CH2:11][C:22]1[CH:32]=[CH:31][C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:24][CH:23]=1)=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 954261Ethyl 4-(bromomethyl)benzoateHCID 15312034AR-260HCID 23665647Potassium tert-butoxide

Product 1

HCID 9861133Ethyl 4-(2-formyl-3-hydroxyphenoxymethyl)benzoate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of 2-hydroxy-6-methoxymethoxybenzaldehyde (0.91 g, 5.1 mM) in dry dimethyl sulphoxide (8 ml) was added potassium t-butoxide (0.57 g, 5.1 mM) with exclusion of moisture. After 10 mins, ethyl 4-bromomethylbenzoate (1.22 g, 5 mM) was added and the whole stirred at room temperature (18 hrs). The reaction mixture was poured into water (100 ml) and the liberated oil extracted into ether. The combined extracts were washed with 5% sodium carbonate solution, water, dried (sodium sulphate) and evaporated. The residual oil (ethyl 4-(2-formyl-3-methoxymethoxyphenoxymethyl)benzoate was dissolved in ethanol (30 ml) and treated with 3 M hydrochloric acid (30 ml) with stirring at 60° C. (30 mins). The solid was filtered off, washed with water, dried, and recrystallised from ethanol/water to give ethyl 4-(2-formyl-3-hydroxyphenoxymethyl)benzoate, m.p. 105°-ω° C. (identical to a sample previously prepared, Example 5(B)).

Workup

  1. extractionthe liberated oil extracted into ether
  2. washThe combined extracts were washed with 5% sodium carbonate solution, water
  3. dry with materialdried (sodium sulphate)
  4. customevaporated
  5. dissolutionThe residual oil (ethyl 4-(2-formyl-3-methoxymethoxyphenoxymethyl)benzoate was dissolved in ethanol (30 ml)
  6. additiontreated with 3 M hydrochloric acid (30 ml)
  7. stirringwith stirring at 60° C. (30 mins)
  8. filtrationThe solid was filtered off
  9. washwashed with water
  10. customdried
  11. customrecrystallised from ethanol/water

Sources & evidence

ORD record
ord-052949e770eb41f985c1ab10e72457d6
Source dataset
uspto-grants-1985_08
Patent number
US04535183

Reaction notes

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