Acetaldehyde → 1-Chloroethyl benzoate

By the procedure of the preceding Preparation, freshly distilled benzoyl chloride (58.0 mL, 70.3 g, 500 mmole) was reacted with acetaldehyde (27.9 mL, 22.0 g, 500 mmol), added at a rate such that the reaction temperature did not exceed 5° C. during the addition. When the addition was complete, the orange solution was allowed to warm to room temperature, then treated with water (100 mL) and methylene chloride (100 mL). The pH was adjusted to 7.0 and the organic layer was isolated, washed with water (100 mL), brine (100 mL), dried (Na2SO4) and concentrated in vacuo to a dark brown oil (83.0 g). 1H NMR indicated less than 0.5% hexanoyl chloride in the product mixture. TLC (CH2Cl2) showed two UV active spots (Rf 0.60, 0.65). A 10.0 g aliquot of the oil was chromatographed on silica gel (methylene chloride) affording 7.3 g of title product as the less polar (Rf 0.65 ) component: 1H NMR (CDCl3) 1.88 (d, J=6 Hz, 3H), 6.78 (q, J=6 Hz, 1H), 7.15-7.70 (m, 3H), 7.70-8.20 (m, 2H).

1. additionadded at a rate such that the reaction temperature
2. additiondid not exceed 5° C. during the addition
3. additionWhen the addition
4. customthe organic layer was isolated
5. washwashed with water (100 mL), brine (100 mL)
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated in vacuo to a dark brown oil (83.0 g)
8. customA 10.0 g aliquot of the oil was chromatographed on silica gel (methylene chloride)

ORD record

ord-64f909737d9843c58f3b9df8f5bf6943

Source dataset

uspto-grants-1985_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04551452