Acetic Acid → 2-(3,4-Dichlorophenyl)-3-(1,3-dioxolan-2-yl)propan-1-ol

HRID 1533035Notes

Reaction equation

[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]([CH2:14][CH:15]2[O:19][CH2:18][CH2:17][O:16]2)[CH:12]=[O:13])[CH:7]=[CH:8][C:9]=1[Cl:10].C(O)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O.ClCCl>[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]([CH2:14][CH:15]2[O:16][CH2:17][CH2:18][O:19]2)[CH2:12][OH:13])[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium borohydride (5 g) was added in two portions, over 40 minutes, to an ice-cooled solution of 2-(3,4-dichlorophenyl)-3-(1,3-dioxolan-2-yl)propan-1-al (53.5 g) (see Preparation 14) in ethanol (300 ml). The mixture was stirred for a further 30 minutes before removing the solvent under reduced pressure to give a residue. This was suspended in water (200 ml), cooled to 0° C. and the mixture acidified (pH<6) with glacial acetic acid. Dichloromethane was added and the aqueous phase basified (pH>8) by addition of solid sodium carbonate. A further amount of dichloromethane (200 ml) was added and the organic and aqueous phases separated. The aqueous phase was further extracted with dichloromethane (200 ml). The organic phases were combined, washed with brine, dried over anhydrous sodium sulphate and the solvent removed under reduced pressure to give 2-(3,4-dichlorophenyl)-3-(1,3-dioxolan-2-yl)propan-1-ol (54.6 g) as a yellow oil.

Workup

custombefore removing the solvent under reduced pressure
customto give a residue
customthe organic and aqueous phases separated
extractionThe aqueous phase was further extracted with dichloromethane (200 ml)
washwashed with brine
dry with materialdried over anhydrous sodium sulphate
customthe solvent removed under reduced pressure

Sources & evidence

ORD record: ord-c5824070b2af41418c50b93b9a37018f
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06207678B1

Reaction notes

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