Acetic Acid → 4-Benzyloxy-3-benzyloxymethylbutanal

HRID 2291846Notes

Reaction equation

HRID 2291846 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([CH2:20][CH:21](OC)[O:22]C)[CH2:11][O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.O>C1COCC1>[CH2:13]([O:12][CH2:11][CH:10]([CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:20][CH:21]=[O:22])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 14843250Benzyl 2-benzyloxymethyl-4,4-dimethoxybutyl ether

Product 1

HCID 113240024-Benzyloxy-3-benzyloxymethylbutanal

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of benzyl 2-benzyloxymethyl-4,4-dimethoxybutyl ether (51.62 g, 0.15 mol), acetic acid (70 ml), water (30 ml), and THF (100 ml) was refluxed for 2 h and then evaporated in vacuum. The residue was dissolved in ether and the solution washed with aqueous potassium carbonate solution and water, dried (MgSO4), and evaporated in vacuum. The residue of crude 4-benzyloxy-3-benzyloxymethylbutanal (quantitative yield) was dissolved in 100 ml of THF and added during 30 min. to a suspension of lithium aluminum hydride (7.6 g, 0.20 mol) in 100 ml of THF. Then 8 ml of water, 8 ml of 15% aqueous NaOH and 24 ml of water were added and the mixture was stirred until a white, sandy suspension was obtained. The inorganic salts were filtered off and washed with several portions of THF. The combined extracts were evaporated in vacuum to yield 41.93 g (93%) of the title compound.

Workup

  1. temperaturewas refluxed for 2 h
  2. customevaporated in vacuum
  3. dissolutionThe residue was dissolved in ether
  4. washthe solution washed with aqueous potassium carbonate solution and water
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuum

Sources & evidence

ORD record
ord-b9a7ee804c23484899254ca285bd8174
Source dataset
uspto-grants-1989_01
Patent number
US04798833

Reaction notes

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