3-chloro-4,6-dihydroxy-2-methylbenzaldehyde

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-Chloro-2,4-dihydroxy-6-methylbenzaldehyde (112 mg, 0.60 mmol) described in M. M. Joullie et al., J. Org. Chem., 50, 3997 (1985), dodecanal (133 mg, 0.72 mmol) and calcium chloride dihydrate (58 mg, 0.40 mmol) were stirred in a 0.4 M potassium hydroxide methanol solution (2 ml) at 0° C. for 24 hours. The reaction mixture was made acidic with 1 M hydrochloric acid, extracted with ethyl acetate, and after post-treatment, the crude product was purified by silica gel thin-layer chromatography (chloroform:ethyl acetate=15:1) to obtain 5-chloro-2,4-dihydroxy-6-methylbenzaldehyde (68 mg, recovery 61%) and 5-chloro-2,4-dihydroxy-3-(1-hydroxydodecyl)-6-methylbenzaldehyde (45 mg, yield 20%). extracted with ethyl acetate after post-treatment, the crude product was purified by silica gel thin-layer chromatography (chloroform:ethyl acetate=15:1)