Ethyl chloroformate → 2-[4-(4-Chlorophenoxy)-phenoxy]-propanol

HRID 2072325Notes

Reaction equation

[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:18]=[CH:17][C:10]([O:11][CH:12]([CH3:16])[C:13](O)=[O:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C(OC(Cl)=O)C.ClC1C=CC(OC2C=CC(OCCC(=O)OC(=O)OCC)=CC=2)=CC=1.[BH4-].[Na+]>O.C1COCC1.C(N(CC)CC)C>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:18]=[CH:17][C:10]([O:11][CH:12]([CH3:16])[CH2:13][OH:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -10 °C

Procedure

13.8 ml. of triethylamine are added, at 10° C., to a solution of 29.25 g. of 2-[4-(4-chlorophenoxy)-phenoxy]-propionic acid in 200 ml. of THF. The mixture is cooled to -10° C., a solution of 9.8 ml. of chloroformic acid ethyl ester in 60 ml, of THF is added dropwise and the mixture is stirred for 1 hour at -10° C. The solution contains 1-[4-(4-chlorophenoxy)-phenoxy]-4,6-dioxa-octane-3,5-dione, which is not isolated. 7.4 g. of NaBH4 are then introduced in portions. The mixture is stirred for 30 minutes at -10° C. and for 30 minutes at 0° C., poured into water and extracted with chloroform. After evaporation of the extract, the residue is boiled for 1 hour with 200 ml. of 6% ethanolic potassium hydroxide solution, the mixture is evaporated and worked up with water and ether to give 2-[4-(4-chlorophenoxy)-phenoxy]-propanol.

Workup

customis not isolated
stirringThe mixture is stirred for 30 minutes at -10° C. and for 30 minutes at 0° C.
extractionextracted with chloroform
customAfter evaporation of the extract
waitthe residue is boiled for 1 hour with 200 ml
customof 6% ethanolic potassium hydroxide solution, the mixture is evaporated

Sources & evidence

ORD record: ord-63370db10b934f7f87837effbdc87571
Source dataset: uspto-grants-1977_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04051173

Reaction notes

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