4-Hydroxybenzaldehyde → 4-(2,2-Diethoxyethoxy)benzaldehyde

HRID 1633159Notes

Reaction equation

HRID 1633159 reaction equation
[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5]Br)[CH3:2].[OH:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1>CN1CCCC1=O.C(OCC)C>[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1)[CH3:2]

Participants

5

Reactant 2

HCID 1264-HydroxybenzaldehydeHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 187608894-(2,2-Diethoxyethoxy)benzaldehydeYield 97%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Bromoacetaldehyde-diethyl-acetal (98.5 g, 0.5 m) and p-hydroxybenzaldehyde (76.4 g, 0.63 m) were dissolved in N-methylpyrrolidone (250 cm3) and heated at 120° for 12 hours. The reaction mixture was cooled, diluted with diethyl ether and the ether layer was extracted four times with 5% sodium hydroxide solution to remove excess of p-hydroxybenzaldehyde. The ether was removed and the product distilled under reduced pressure to give 115 g (97%) of p-formylphenoxy-acetaldehyde-diethyl-acetal, b. 139°-140°/1.5 mbs. Acetylbenzene-sulphonic acid (sodium salt, 40 g, 0.18 m) was dispersed in a mixture of methanol (400 cm3) and 10% aqueous sodium hydroxide (150 cm3).

Workup

  1. temperatureheated at 120° for 12 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionthe ether layer was extracted four times with 5% sodium hydroxide solution
  4. customto remove excess of p-hydroxybenzaldehyde
  5. customThe ether was removed
  6. distillationthe product distilled under reduced pressure

Sources & evidence

ORD record
ord-dfc82f4a1af0443da29e9e3424f567a3
Source dataset
uspto-grants-1984_10
Patent number
US04478977

Reaction notes

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