Hydrochloric Acid → (+/-)-2-[4-(cis-2-Hydroxycyclohexylmethyl)phenyl]propionic acid

HRID 1982183Notes

Reaction equation

[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH3:19])[C:16]([OH:18])=[O:17])=[CH:11][CH:10]=1.CCC(C)[BH-](C(C)CC)C(C)CC.[K+].Cl>O1CCCC1>[OH:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]([CH3:19])[C:16]([OH:18])=[O:17])=[CH:13][CH:14]=1

Participants

Conditions

Temperature: -78 °C

Procedure

10.0 g of (±)-2-[4-(2-oxocyclohexylmethyl)phenyl]-propionic acid were dissolved in 150 ml of tetrahydrofuran. The solution was cooled to -78° C. and, whilst maintaining the solution at this temperature and under a stream of nitrogen, 200 ml of K-Selectride (as a 0.5 molar tetrahydrofuran solution) were added dropwise. When the whole of the K-Selectride had been added, the reaction mixture was stirred for 1 hour at 0° C., after which it was cooled to -10° C. and 400 ml of a 0.5N solution of hydrochloric acid was added through a dropping funnel. The reaction mixture was stirred for 1 hour, after which it was extracted with diethyl ether. The extract was washed with water and dried over anhydrous sodium sulphate. The solvent was distilled off, giving 10.5 g of the title compound in the form of crystals. These were recrystallised from a mixture of diethyl ether and hexane, giving the title compound as pure crystals melting at 130°-133° C.

Workup

temperaturewhilst maintaining the solution at this temperature
temperatureafter which it was cooled to -10° C.
stirringThe reaction mixture was stirred for 1 hour
extractionafter which it was extracted with diethyl ether
washThe extract was washed with water
dry with materialdried over anhydrous sodium sulphate
distillationThe solvent was distilled off

Sources & evidence

ORD record: ord-4fcc628d12684d4ba630e1032f91d2b9
Source dataset: uspto-grants-1986_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04595699

Reaction notes

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