Acetic Acid → 4-Benzyloxy-3-benzyloxymethylbutanal

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

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.