1-Bromo-3-chloropropane → HCID 23036250, compound

HRID 1709868Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:17][CH2:18][CH2:19][Cl:20].C(=O)([O-])[O-].[K+].[K+]>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH2:17][CH2:18][CH2:19][Cl:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 80061-Bromo-3-chloropropane

HCID 11430Potassium Carbonate

HCID 804592-Benzyloxyphenol

Product 1

HCID 23036250HCID 23036250, compoundYield 97.1%

Procedure

A mixture of 50 g (0.25 mole) of 2-benzyloxyphenol, 78.7 g (0.5 mole) of 1-bromo-3-chloropropane and 103.7 g of anhydrous potassium carbonate in 1 liter of actone was heated at reflux for 24 hr. The reaction mixture was cooled, filtered and concentrated in vacuo to give 67.2 g of a tan oil as residue. The oil was dissolved in 300 ml of ethyl ether and washed with 100 ml of a 5% sodium hydroxide solution. A solid precipitated, about 200 ml of water was added and the precipitated sold redissolved. Solvent layers were separated and the ethyl ether layer washed twice with a 5% sodium hydroxide solution. The organic layer was next washed with water, brine, and dried over sodium sulfate and concentrated to give 58.4 g (84%) of oil as product.

Workup

temperaturewas heated
temperatureat reflux for 24 hr
temperatureThe reaction mixture was cooled
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-8e19195ff66b455e8f724d0d65550f80
Source dataset: uspto-grants-1990_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04950674

Reaction notes

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