Methanol → 2,3-Dichlorobenzyl alcohol

To solution of MeOH (150 ml) containing 2,3-dichlorobenzaldehyde (20 g, 0.11 mole), cooled in ice bath, was added a solution of NaBH4 (4.54 g, 0.12 mole) in 0.2 M NaOH (15 mL) slowly over 15 min under nitrogen atmosphere. After completion of the addition, the mixture was allowed to warm up gradually to rt, and stirred for 2.5 h at rt. The reaction was quenched by cooling the mixture and pouring it slowly to ice water (˜700 mL). The mixing led to formation of white precipitates. After stirring for 30 min. the precipitates were collected on Bòcbner funnel, and the collected solid was dissolved in EtOAc (200 mL). The organic solution was washed with 0.1 M NaOH (150 mL), dried over Na2SO4, and concentrated to dryness in vacuo, yielding 2,3-dichlorobenzylalcohol as white solid (19.57 g, 97%). Rf=0.46 in EtOAc/hexane (1/3). 1H-NMR (CD3OD, 299.96 MHz: δ (ppm) 7.52-7.49 (dd, 1H), 7.45-7.42 (dd, 1H), 7.33-7.27 (t, 1H), 4.70 (s, 2H). Retention time (anal. HPLC: 10 to 70% MeCN/H2O over 6 min)=4.00 min.

1. temperaturecooled in ice bath
2. additionAfter completion of the addition
3. customThe reaction was quenched
4. temperatureby cooling the mixture
5. additionpouring it slowly to ice water (˜700 mL)
6. stirringAfter stirring for 30 min. the precipitates
7. customwere collected on Bòcbner funnel
8. dissolutionthe collected solid was dissolved in EtOAc (200 mL)
9. washThe organic solution was washed with 0.1 M NaOH (150 mL)
10. dry with materialdried over Na2SO4
11. concentrationconcentrated to dryness in vacuo

ORD record

ord-da51d8e7dec1499ebf6d2f0f4e124c47

Source dataset

uspto-grants-2002_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06479498B1